O-benzyloxime ethers and crop protection agents containing these compounds

ABSTRACT

O-Benzyloxime ethers of the formula I ##STR1## where X is substituted or unsubstituted CH 2 , NOalkyl 
     Y is 
     O, S, NR 5   
     R 1 , R 2 , R 5  are H, alkyl 
     Z 1 , Z 2  are H, halogen, methyl, methoxy, cyano 
     R 3 , R 4  are hydrogen, cyano, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, 
     N(R 6 ) 2 , where R 6  is H, alkyl, substituted or unsubstituted phenyl, 
     --CO--N(R 7 ) 2 , where R 7  is H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyloxy, 
     R 3  and R 4  together may form a carbocyclic or heterocyclic ring which is substituted or unsubstituted, and 
     R 3  or R 4  may be halogen, or ##STR2## may be ##STR3## where n is an integer from 1 to 4, and 
     R 8  is, or, when n&gt;1, the RB&#39;s are identical or different and are each, H, halogen, cyano, nitro or substituted or unsubstituted C 1  -C 4  -alkyl, C 1  -C 4  -alkoxy, C 1  -C 4  -haloalkyl, C 1  -C 4  -haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy, 
     and crop protection agents containing these compounds.

This is a DIVISION of application Ser. No. 07/962,340 filed on Oct. 15, 1992, now U.S. Pat. No. 5,292,759, which is a division of application Ser. No. 07/722,209 filed on Jun. 27, 1991, now U.S. Pat. No. 5,194,662.

The present invention relates to novel O-benzyloxime ethers and a method for controlling pests, in particular fungi, insects, nematodes and spider mites with these compounds.

It is known that substituted phenylacetic acid oxime derivatives can be used as fungicides (European Patent 253,213). However, their action is unsatisfactory.

We have found, surprisingly, that O-benzyloxime ethers of the general formula I ##STR4## where

X is CH₂, CH--C₁ --C₄ -alkyl, CH--C₁ --C₄ -alkoxy, CH--C₁ -C₄ -alkylthio or N--C₁ -C₄ -alkoxy,

Y is O, S or NR⁵,

R¹, R² and R⁵ are each H or C₁ -C₄ -alkyl,

Z¹ and Z² are identical or different and are each H, halogen, methyl, methoxy or cyano,

R³ and R⁴ are identical or different and are each hydrogen, cyano, straight-chain or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₅ -haloalkenyl, C₂ -C₆ -cycloalkenyl, C₁ -C₆ -halocycloalkenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₄ -alkylthio, benzylthio, C₁ -C₄ -alkylcarbonyl, unsubstituted or substituted phenylcarbonyl, unsubstituted or substituted benzylcarbonyl, C₁ -C₄ -alkoxycarbonyl, unsubstituted or substituted phenoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted aryl-C₁ -C₄ -alkyl, unsubstituted or substituted aryl-C₁ -C₄ -alkenyl, unsubstituted or substituted aryloxy-C₁ -C₄ -alkyl, unsubstituted or substituted arylthio-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryloxy, unsubstituted or substituted hetarylthio, unsubstituted or substituted hetaryl-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl-C₂ -C₄ -alkenyl unsubstituted or substituted hetaryl-oxy-C₁ -C₄ -alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyloxy, N(R⁶)₂, where the radicals R⁶ are identical or different and are each H, C₁ -C⁶ -alkyl or unsubstituted or substituted phenyl, or

--CO--N(R⁷)₂, where the radicals R⁷ are identical or different and are each H or C₁ -C₄ -alkyl, substituents, in addition to hydrogen, being halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₁₀ -alkoximino-C₁ -- or C₂ -alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C₃ -C₆ -cycloalkyl, heterocyclyl or heterocyclyloxy, or

R³ and R⁴ together may form a carbocyclic or heterocyclic ring which may be substituted by the abovementioned substituents, and R³ or R⁴ may be halogen, or ##STR5## may be ##STR6## where

n is an integer from 1 to 4, and

R⁸ is, or, when n>1, the R⁸ 's are identical or different and are each, H, halogen, cyano, nitro substituted or unsubstituted C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl: hetaryloxy, have excellent fungicidal, insecticidal, nematicidal and acaricidal activity which is better than that of the known phenylacetic acid derivatives.

The fungicidal action is preferred.

The radicals stated for the general formula I may, for example, have the following meanings:

X may be C₁ -C₄ -alkylidene (eg. methylidene, ethylidene, n-or isopropylidene, n-, iso-, sec- or tert-butylidene), C₁ -C₄ -alkoxymethylidene (eg. methoxy-, ethoxy-, n-propoxy, isopropoxy-, n-butoxy-, isobutoxy-, sec-butoxy- or tertbutoxymethylidene), C₁ -C₄ -alkylthiomethylidene (eg. methyl-, ethyl-, n-propyl-, isopropyl-, n-butylthio-, isobutylthio-, sec-butylthio- or tert-butylthiomethylidene or C₁ -C₄ -alkoximino (eg. methoximino, ethoximino, n-propoximino, isopropoximino, n-butoximino, isobutoximino, sec-butoximino or tert-butoximino),

Y may be O, S or NR⁵,

R¹, R² and R⁵ may each be H or C₁ -C₄ -alkyl (eg. methyl, ethyl, n- or isopropyl, n- or iso-, sec- or tert-butyl),

Z¹ and Z² may be H, halogen (eg. fluorine, chlorine, bromine or iodine ), methyl, methoxy or cyano, and

R³ and R⁴ may be identical or different and are each hydrogen, cyano, straight-chain or branched C₁ -C₁₀ -alkyl (eg. methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec-, tert- or neopentyl, n-hexyl or n-decyl), C₁ -C₄ -haloalkyl (eg. trifluoromethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, fluorodichloromethyl, difluorochloromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl or pentachloroethyl),

C₃ -C₆ -cycloalkyl ( eg. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl),

C₃ -C₆ -halocycloalkyl (eg. 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-dichloro-3-methylcyclopropyl or tetrafluorocyclobutyl),

C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl (eg. 1-methylcyclopropyl, 2,2-dimethylcyclopropyl or 1-methylcyclohexyl),

C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl (eg. methoxymethyl, ethoxymethyl, n- or isopropoxymethyl, n-, iso-, sec- or tert-butoxymethyl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, 2-n- or isopropoxyprop-2-yl or 2-n-, iso-, sec- or tert-butoxyprop-2-yl), C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl (eg. methylthiomethyl, ethylthiomethyl, n- or isopropylthiomethyl, n-, iso-, sec- or tert-butylthiomethyl, 2-methylthioprop-2-yl, 2-ethylthio-prop-2-n-yl 2-n- or isopropylthioprop-2-yl or 2-n, iso-, sec- or tert-butylthioprop-2-yl),

aryl(phenyl)thio-C₁ -C₄ -alkyl (eg. phenylthiomethyl or 2-chlorophenylthiomethyl),

C₂ -C₆ -alkenyl (eg. vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 3-methyl-2-butenyl or 2-methyl-2-penten-5-yl),

C₂ -C₅ -haloalkenyl (eg. 2,2-difluorovinyl, 2,2-dichlorovinyl, 3,3,3-trifluoropropenyl, 3,3,3-trichloropropenyl or 3-chloro-2-propenyl),

C₃ -C₆ -cycloalkenyl (eg. cyclopent-1-enyl, cyclopentadienyl or cyclohex-1-enyl),

C₃ -C₆ -halocycloalkenyl (eg. pentafluorocyclopentadienyl or pentachlorocyclopentadienyl),

C₂ -C₄ -alkynyl (eg. ethynyl, 1-propynyl or 1-propargyl),

C₁ -C₄ -alkoxy (eg. methoxy, ethoxy, n- or isopropoxy or n-, iso-, sec- or tert-butoxy),

C₁ -C₄ -alkylthio (eg. methylthio, ethylthio, n- or isopropylthio or n-, iso-, sec-or tert-butylthio)or benzylthio,

C₁ -C₄ -haloalkoxy (eg. trifluoromethoxy, pentafluoroethoxy or 1,1,2,2-tetrafluoroethoxy),

N(R⁶)₂ (eg. amino, methylamino, dimethylamino, ethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino or diisobutylamino),

C₁ -C₄ -alkylcarbonyl (eg. acetyl, propionyl, butyryl, isobutyryl or pivaloyl),

unsubstituted or substituted phenylcarbonyl (eg. benzoyl or 4-chlorobenzoyl),

unsubstituted or substituted benzylcarbonyl (eg. benzylcarbonyl), C₁ -C₄ -alkoxycarbonyl (eg. metbozycarbonyl, etbozycarbonyl, n- or isopropoxycarbonyl or n-, iso-, sec- or tertbutoxycarbonyl),

unsubstituted or substituted phenoxycarbonyl (eg. phenoxycarbonyl or 4-chlorophenoxycarbonyl), unsubstituted or substituted benzyloxycarbonyl (eg. benzyloxycarbonyl),

--CO--N(R⁷)₂ (eg. aminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, diisopropylaminocarbonyl, phenylaminocarbonyl or N-methyl-N-phenylaminocarbonyl), unsubstituted or substituted aryl (eg. phenyl, naphthyl or anthryl),

unsubstituted or substituted aryloxy (eg. phenoxy, naphthyloxy or anthryloxy),

unsubstituted or substituted arylthio (eg. phenylthio), unsubstituted or substituted aryl-C₁ -C₄ -alkyl (eg. benzyl, 1-phenethyl, 2-phenethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 2-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl or 4-phenylbutyl),

unsubstituted or substituted aryl-C₁ -C₄ -alkenyl (eg. phenyl-1-ethenyl, 2-phenyl-1-propenyl, 2,2-diphenylethenyl, 1-phenyl-1-propen-2-yl or 1-phenyl-1-ethenyl), unsubstituted or substituted aryloxy-C₁ -C₄ -alkyl (eg. phenoxymethyl),

unsubstituted or substituted arylthio-C₁ -C₄ -alkyl (eg. phenylthiomethyl),

unsubstituted or substituted hetaryl (eg. pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, 2,6-pyrimidinyl, 1,5-pyrimidinyl, thienyl, 2-thienyl, 3-thienyl, furyl, 2-furyl, 3-furyl, 1-pyrrolyl, 1-imidazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, 4-thiazolyl or 2-benzothiazolyl),

unsubstituted or substituted hetaryloxy (eg. 2-pyridyloxy or 2-pyrimidinyloxy),

unsubstituted or substituted hetarylthio (eg. 2-pyridylthio, 2-pyrimidinylthio or 2-benzothiazolylthio),

unsubstituted or substituted hetaryl-C₁ -C₄ -alkyl (eg. 2-pyridylmethyl or 3-pyridylmethyl),

unsubstituted or substituted hetaryloxy-C₁ -C₄ -alkyl (eg. furfurylmethoxy, thienylmethoxy, 3-isoxazolylmethoxy, 2-oxazolylmethoxy or 2-pyridylmethoxy),

unsubstituted or substituted hetaryl-C₂ -C₄ -alkenyl (eg. 2'-furyl-2-ethenyl, 2'-thienyl-2-ethenyl or 3'-pyridyl-2-ethenyl), unsubstituted or substituted heterocyclyl (eg. oxiranyl, 1-aziridinyl, 1-azetidinyl, 1-pyrrolidinyl, 2-tetrahydrofuryl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 1-piperidinyl, 1-morpholinyl, 1-piperazinyl, 1,3-dioxanyl or 3-tetrahydrothiopyranyl) or unsubstituted or substituted heterocyclyloxy (eg. 2dihydropyranyloxy or 2-tetrahydropyranyloxy).

The radicals referred to above in connection with unsubstituted or substituted are, in addition to hydrogen, for example, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, methoximinomethyl, ethoximinomethyl, n-propoximinomethyl, n-butoximinomethyl, n-pentyloximinomethyl, n-hexyloximinomethyl, allyloximinomethyl, benzyloximinomethyl, isopropoximinomethyl, isobutoximinomethyl, tert-butoximinomethyl, methylimino- 1-ethyl, ethoximino- 1-ethyl, n-propoximino-1-ethyl, n-butoximino-1-ethyl, n-pentyloximino-1-ethyl, n-hexyloximino-l-ethyl, allyloximino-1-ethyl, benzyloximino-1-ethyl, phenyl, phenoxy, benzylory, imidazol-1-yl, piperazin-1-yl, 4-morpholinyl, piperidin-1-yl, pyrid-2-yloxy, cyclopropyl, cyclohexyl, oxiranyl, 1,3-dioxan-2-yl, 1,3-dioxolan-2-yl and tetrahydropyran-2-yloxy.

The group ##STR7## may also be the radical of a carbocyclic or heterocyclic oxime (eg. cyclopentanone oxime, cyclohexanone oxime, cycloheptanone oxime, 2-adamantanone oxime, D-camphor oxime, 1-tetralone oxime, 1-indanone oxime, 9-fluorenone oxime, 1-methyl-4-piperidone oxime, violuric acid or N,N-dimethylvioluric acid).

R³ and R⁴ together then form, for example, a cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralin, indane or fluorene ring.

One of the radicals R³ or R⁴ may furthermore be halogen (eg. fluorine, chlorine, bromine or iodine).

n may be 1, 2, 3 or 4 and R⁸ may be for example H, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethoxy, 1,1,2,2-tetrafluoromethoxy, phenyl, phenoxy, benzyloxy or pyrid-2-yl, where these radicals in turn may be substituted by fluorine, chlorine, bromine, iodine, cyano, methyl or methoxy.

Among the compounds in which R³ and R⁴ are hydrogen, the preferred compounds are those in which either only R³ or only R⁴ is hydrogen, in particular the compounds in which R³ is hydrogen.

Also preferred are compounds of the formula II in which X is CH₂, CHCH₃, CHC₂ H₅, CHOCH₃, CHOC₂ HS, CHSCH₃ or CHSC₂ H₅, Y is O, R¹ is C₁ -C₄ -alkyl, R² is H or methyl, R³ and R⁴ are identical or different and each is hydrogen, cyano, straight-chain or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₆ -alkoxy-C₁ 14 C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₂ -C₄ -haloalkenyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁ -C₄ -alkyl, substituted or unsubstituted aryl-C₂ -C₄, alkenyl, substituted or unsubstituted aryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio or substituted or unsubstituted heterocyclyl, or each is N(R⁶)₂, R⁶ being identical or different and denoting H, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl or substituted or unsubstituted phenyl, or each is --CO--N(R⁷)₂, R⁷ being identical or different and denoting H or C₁ -C₄ -alkyl, the term "substituted" denoting the radicals listed in claim 1, and R³ and R⁴ may together denote a carbocyclic or heterocyclic ring which may be substituted by the radicals given under "substituted", and R³ and R⁴ may be halogen, and Z¹ and Z² are hydrogen, fluorine, chlorine, bromine, iodine, methyl, cyano or methoxy.

Owing to the C═C or C═N double bonds, the novel compounds of the general formula I may be obtained in the preparation as E/Z isomer mixtures. These can be separated into the individual components in a conventional manner, for example by crystallization or chromatography.

Both the individual isomeric compounds and mixtures thereof form subjects of the invention and can be used as pesticides.

The compounds of the general formula I as claimed in claim i are prepared, for example, as described in Scheme 1 (Z¹ and Z² are each H). ##STR8##

The compounds of the general formula I in which X is CH₂, CH-alkyl or CH-alkoxy can be prepared, for example, from the ketoesters 4 by a Witrig or WittigHorner reaction (cf. European Patents 348,766 and 178,826 and DE 3 705 389). The similar compounds 5 are likewise obtained from the ketoesters 2.

Alternatively, it is also possible to adopt a procedure in which compounds of the formula 7 or 9 are condensed with suitable reagents, for example with formaldehyde where X is CH₂ (cf. DE 3317356), a) with aldehydes (cf. D. M. Brown, J. Chem. Soc. 1948, 2147) or b) first with N,N-dimethylformamide dimethyl acetal, followed by reaction with a Grignard reagent (similarly to C. Jutz, Chem. Bet. 91 (1958), 1867) where X is CH-alkyl, or with a formate followed by alkylation (cf. European Patent 178,826) where X is CH-O-alkyl. Further preparation methods for the compounds of the formula 5 and I where X is CH--O--alkyl are described in European Patent 178,826.

Another possible method for preparing the compounds of the formula I where X is CH-alkyl and YR₂ is COOAlk is to react ketene acetals with phenylchlorocarbenes (S. N. Slougui and G. Rousseau, Synth. Commun. 12 (5) (1982), 401-407).

For compounds of the general formula I where X is CH--S--alkyl, the preparation can be carried out by the methods described in European Patents 244,077 or 310,954.

The intermediates of the formulae 3, 6 and 8 can be prepared from the compounds 2, 5 and 7 by halogenating the latter by a known method, for example with chlorine, bromine or N-bromosuccinimide, in an inert solvent (eg. CCl₄ or cyclohexane), with exposure to, for example, a Hg vapor lamp or in the presence of a free radical initiator, eg. dibenzoyl peroxide, or by introducing the radicals L, eg. mesylate, rosylate, acetate or triflate, via suitable intermediates (where L is halogen or OH).

The oxime ethers of the formula I where X is N-Oalkyl can be prepared from 4 a) by reaction with an O-alkylhydroxylamine hydrochloride or b) with hydroxylamine hydrochloride and subsequent alkylation with an alkylating agent (eg. an alkyl iodide, dialkyl sulfate, etc.) (cf. DE 3 623 921).

Furthermore, a phenylacetic ester of the formula 9 can be converted with a base (eg. NaOMe, NaH, K tert-burylate, etc.) in a solvent (eg. diethyl ether, toluene, tert-butanol, etc.) by a method similar to that in European Patent 254,426 into its anion and can be converted into the oxime with a suitable nitrosating agent (such as methyl nitrite, amyl nitrate, tert-butyl nitrite, etc.). The resulting oximate is alkylated with an alkylating agent (eg. an alkyl iodide or dialkyl sulfate).

The same processes can also be applied to the compounds of the formulae 2 and 7, and the resulting oxime ethers 5 can be converted in a known manner (European Patent 254,426) via the intermediates 6 (L is, for example, halogen).into the desired compounds I.

In the preparation processes described above, Y--R¹ is usually alkoxy.

The compounds in which YR¹ is OH (11) can be prepared by methods known from the literature (Organikum 16th edition, pages 415 and 622), from the compounds of the general formula I where YR¹ is COOAlkyl (10) (cf. Scheme 2): ##STR9##

Alternatively, the nitriles 12 can be converted in a known manner (cf. Organikum 16th edition, page 424 et seq. (1985) into the carboxylic acids 11.

The resulting carboxylic acids 11 can be converted in a conventional manner into the acyl chlorides 14 (cf. Organikum 16th edition, page 423 et seq. (1985). The conversion of 14 into the amides 15 is effected by methods similar to that described in Organikum 16th edition, page 412 (1985).

The thioesters 13 are obtained from the acyl chlorides 14 (similarly to Houben-Weyl Vol. 8, page 464 et seq. (1952)).

Alternatively, the thioesters 13 can also be prepared from the acids 11 (similarly to Houben-Weyl Vol. E5, page 855 et seq. (1985)).

The amides 15 in which R¹ and R⁵ are each H can also be prepared from the nitriles 12 by processes known from the literature (cf. Synthesis 1980, 243).

The preparation of the compounds of the general formulae 2 and 7 with ortho-methyl substitution at the aromatic (R² =H) is known.

(YR¹ =OAlkyl; cf. European Patents 178,826 and 260,832).

The oximes required for the preparation of the compounds of the general formula I are either known or can be prepared by one of the processes shown in Scheme 3. ##STR10##

Methods for the conversion of 16 or 18 into 17 are described in Houben-Weyl, Vol. 10/4 (1968).

Furthermore, aldoximes 19 can be chlorinated by known methods and can be reacted with, for example, a cyanide to give the derivatives 17 (R³ =CN) (cf. M. R. Zimmermann J. f. prakt. Chemie 66 (1902), 359).

The specific derivatives in which R³ is CN and R⁴ is alkoxyalkyl are prepared according to European Patent 74,047, those in which R³ is CN and R⁴ is alkyl-thioalkyl according to European Patent 150,822 and those in which R³ is CN and R⁴ is alkyl according to DE 2 304 848.

The method employing Me₃ SiO--NH--SiMe₃ (R. U. Hoffmann and G. A. Bunrain, Synthesis 1987, 831) is used for sterically hindered ketones. ##STR11##

The novel compounds of the general formula I as claimed in claim 1 are prepared, for example, by a method in which an oxime of the formula 17 is reacted with a substituted benzyl compound 6 in which L is a leaving group (eg. chloride, bromide, p-toluenesulfonate, methanesulfonate, triflate or acetate). R¹ -R⁴, X and Y have the abovementioned meanings.

The reactions described can be carried out, for example, in an inert solvent (eg. acetone, acetonitrile, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone or pyridine) with the use of a base (eg. sodium carbonate, potassium-carbonate, sodium hydroxide, potassium hydroxide, sodiumhydride or sodium methylate).

The reactions can also be carried out in a two-phase system (eg. dichloromethane or water) with the aid of a suitable phase transfer catalyst (eg. cetyltrimethylammonium chloride or benzyltrimethylammonium chloride).

Another method for the preparation of compounds I (YR¹ =OAlkyl, X=CH--OAlkyl or N--OAlkyl and L=Cl, Br, tosylate or mesylate) is illustrated by Scheme 5: ##STR12##

This synthesis sequence is carried out, as far as compound 22, similarly to the methods described in European Patent 244,786.

For example, N-hydroxyphthalimide can be converted with a halide or sulfonic ester 6 in the presence of an acid acceptor (eg. triethylamine, potassium carbonate, etc.), in a suitable solvent (eg. N-methylpyrrolidone, dimethylformamide, etc.), into the imidoether 21.

Cleavage to give the O-substituted hydroxylamine 22 can be effected with a mineral acid (eg. HCl; cf. Houben-Weyl Vol. 10/1, page 1181 et seq.) or with a base (for example with hydrazine or ethanolamine).

The conversion of amine 22 to I is carried out in a conventional manner (cf. D. Otzanak, J.C.S. Chem. Commun. 1986, 903).

The Examples and methods which follow are intended to illustrate the preparation of the novel active ingredients and of the novel intermediates.

Method 1: 3,4-Dichloroacetophenone oxime

12.0 g (0.17 mol) of hydroxylammonium hydrochloride and 18.9 g (0.1 mol) of 3,4-dichloroacetophenone are added to a mixture of 20 ml of H20, 100 ml of methanol and 8 g (0.1 mol) of pyridine. Refluxing is carried out for 1 hour, after which the mixture is acidified with 2N HCl and extracted with 3×100 ml of tert-butyl methyl ether. The organic phase is washed with water, dried with Na₂ SO₄ and evaporated down. 19.6 g (96% of theory) of crystals of melting point 92° C., which according to ¹ H-NMR consist of 90% of trans-oxime, are obtained.

Method 2: 2-Oximino-2-tetrahydropyran-2'-ylacetonitrile

265.4 g (2.05 mol) of tetrahydrofuran-2-carbaldehyde oxime in 2 1 of diethyl ether are initially taken at from -55° to -60° C. 153.5 g (2.15 mol) of chlorine are then passed in and the temperature is increased to -20° C.; stirring is carried out for 1 hour, the mixture is then evaporated down in a rotary evaporator at 10° C., the residue is taken up in 1.5 1 of diethyl ether and the solution is stirred overnight in the absence of light, while cooling with ice. The solution is then filtered and the filtrate is added dropwise, while cooling with ice, to 147.3 g (2.27 mol) of potassium cyanide in 1 l of methanol at 10°-15° C. (exothermic). Stirring is carried out for 5 hours at room temperature (20° C.), after which the precipitate is filtered off under suction and washed twice with diethyl ether. The organic phases are partitioned between tert-butyl methyl ether and water and the residue of the ether phases is crystallized from dichloromethane/n-hexane at 0° C.

After filtration under suction and drying, 208 g (66% of theory) of a spectroscopically pure substance of melting point 105°-106° C. remain.

Method 3: 3-Methoxy-3-methyl-2-oximinobutyronitrile

53.6 g (0.46 mol) of 2-methoxy-2-methylpropionaldehyde oxime in ether (about 1 M) are initially taken at from -5° to -10° C. 35.8 g (0.5 mol) of chlorine gas are passed in, after which stirring is carried out for 1 hour at this temperature and the mixture is then evaporated down at 10° C. and the residue is taken up in diethyl ether. 24.7 g (0.5 mol) of sodium cyanide in 375 ml of 20:1 methanol/H₂ O are initially taken at 10° C. and the above ethereal solution is rapidly added dropwise. After 4 hours at room temperature, the mixture is filtered under suction and the residue is washed with twice 100 ml of methanol. The combined solutions are evaporated down and the residue is partitioned between methyl tert-butyl ether and water. Drying the organic phase over Na₂ SO₄, evaporating down and crystallizing from dichloromethane-/n-hexane give 41.1 g (63% of theory) of a white powder of melting point 102°-104° C.

Method 4 Methyl 3-methoxy-2-[2'-(phthalimido-oxy)-methyl]-phenylacrylate

10 g (35 mmol) of methyl 3-methoxy-2-(2'-bromo-methyl)-phenylacrylate, 5.7 g (35 mmol) of hydroxyphthalimide, 3.9 g (38.6 mmol) of triethylamine and 50 ml of N-methylpyrrolidone are combined and the mixture is stirred for 2 hours at 60° C. It is then poured onto ice water, and the residue is filtered off under suction, washed with water and isopropanol and dried under reduced pressure. 9.0 g (70% of theory) of a crystalline product of melting point 156°-158° C. remain.

¹ H-NMR (CDCl₃): δ=3.60 (s, 3H); 3.75 (s, 3H); 5.12 (s, 2H); 7.13 (dbr, 1H); 7.35 (m, 2H); 7.62 (s, 1H); 7.7-7.9 (m, 5H)

Method 5 Methyl 3-methoxy-2-(2'-aminooxymethyl)-phenylacrylate

10.0 g (27 mmol) of the product from Method 4 are dissolved in 150 ml of methanol and the solution is stirred with 1.4 g (27 mmol) of hydrazine hydrate for 2 hours at room temperature. The precipitate is filtered off under suction, the mother liquor is evaporated down, the residue is stirred with diethyl ether, the precipitate is filtered off under suction again and the mother liquor is evaporated down. 6.0 g (92% of theory) of a yellow oil result (purity according to ¹ H-NMR about 90%). ¹ H-NMR (CDCl₃): δ=3.71 (s, 3H); 3.80 (s, 3H); 4.60 (s, 2H); (5.35 (sbr, 2H); 7.0-7.50 (m, 4H); 7.58 (s, 1H).

Method 6 Methyl 2-methoximino-2-(2'-phthalimidooxymethyl)-phenylacetate

2.0 g (7 mmol) of methyl 2-methoximino-2-(2'-bromomethyl)-phenylacetate, 1.1 g (7 mmol) of hydroxyphthalimide and 0.8 g (7.7. mmol) of triethylamine are dissolved in 10 ml of N-methylpyrrolidone and the solution is stirred for 2 hours at 70° C. For working up, ice water is added, and the crystals are filtered off under suction, washed with water and methyl tert-butyl ether and dried.

1.5 g (58% of theory) of crystals of melting point 152°-155° C. remain.

¹ H-NMR (CDCl₃ : δ=3.83 (s, 3H); 3.98 (s, 3H); 5.07 (s, 2H); 7.15 (dbr, 1H); 7.45 (mc, 2H); 7.60-7.85 (m, 5H)

Method 7 Methyl 2-methoximino-2-(2'-aminooxymethyl)-phenylacetate

15.0 g (41 mmol) of the product from Method 6 are stirred with 2.1 g (42 mmol) of hydrazine hydrate in 150 ml of methanol for 2 hours at room temperature. The residue is again filtered off under suction, the mother liquor is evaporated down and triturated with diethyl ether, the residue is filtered off under suction and the mother liquor is evaporated down. 7.8 g (80% of theory) of an acid-sensitive oil remain.

¹ H-NMR (CDCl₃), δ=3.90 (s, 3H); 4.03 (s, 3H); 4.59 (s, 2H); 5.35 (sbr, 2H); 7.15 (dbr, 1H); 7.40 (sbr, 3H)

EXAMPLE 1 Methyl 3-methoxy-2-[2'-[1-(3"'5"'-dichlorophenyl)-1"-methyl]-iminooxymethyl]-phenylacrylate (No. 582, Table I)

0.6 g (25 mmol) of sodium hydride powder in 100 ml of acetonitrile is initially taken, 5.1 g (25 mmol) of 3,5-dichloroacetophenone oxime are added and the mixture is refluxed for 1 hour. Thereafter, 9.3 g (33 mmol) of methyl 2-(2'-bromomethyl)-phenyl-3-methoxyacrylate in 50 ml of acetonitrile are added dropwise and refluxing is continued for a further 4 hours. The mixture is evaporated down under reduced pressure and then partitioned between methyl tert-butyl ether and saturated ammonium chloride solution, the organic phase is washed with water and the residue obtained by evaporation is crystallized from methyl butyl ether/n-hexane. 4.6 g (45% of theory) of a substance of melting point 87°-88° C. are obtained.

¹ H-NMR (CDCl₃ : δ=2.19 (s, 3H); 3.70 (s, 3H); 3.81 (s, 3H); 5.15 (s, 2H); 7.08 (m, 1H); 7.17 (m, 3H); 7.50 (m, 3H); 7.58 (s, 1H)

EXAMPLE 2 Methyl 3-methoxy-2-[2'-(1"-cyano-(-1"-methoxy-1"-methylethyl)-iminooxymethyl]-phenylacrylate (No. 36, Table I)

3.3 g (23 mmol) of 3-methoxy-3-methyl-2-oximinobutyronitrile, 6.6 g (23 mmol) of methyl 2-(2'-bromomethylphenyl)-3-methoxyacrylate and 3.2 g (23 mmol) of potassium carbonate in 60 ml of N,N-dimethylformamide are stirred for 15 hours at room temperature. The mixture is then evaporated down, the residue is taken up in ethyl acetate, the solution is washed with 3×50 ml of water and the organic phase is dried over sodium sulfate, evaporated down and chromatographed over silica gel using 40:1 toluene/ethyl acetate.

Yield: 7.0 g (88% of theory) of an oil.

IR (film): 1,285, 1,258, 1,189, 1,180, 1,131, 1,111, 1,069, 1,008 cm⁻¹.

EXAMPLE 3 Methyl 2-methoximino-2-[2'-(1"-(3"', 5"'-dichlorophenyl)-1"-methyl)-iminooxymethyl]-phenylacetate (No. 582, Table II)

0.6 g (25 mmol) of NaH in 50 ml of acetonitrile is initially taken, and 5.1 g (25 mmol) of 3,5-dichloroacetophenone oxime are added at room temperature. Refluxing is carried out for 1 hour, after which 9.4 g (33 mmol) of methyl 2-methoximino-2-(2'-bromomethyl)phenylacetate in 50 ml of acetonitrile are added dropwise and refluxing is continued for a further 4 hours. After evaporating down, partitioning the residue between water/methyl tert-butyl ether, washing the organic phase with water, drying the organic phase with sodium sulfate and evaporating down, the residue is subjected to column chromatography over silica gel using methyl tert-butyl ether/hexane. 5.4 g (53% of theory) of crystals of melting point 95°-97° C. result.

¹ H-NMR (CDCl₃): δ=2.17 (s, 3H); 3.82 (s, 3H); 4.02 (s, 3H); 5.15 (s, 2H); 7.20 (dbr, 1H); 7.25-7.55 (m, 6H)

EXAMPLE 4 Methyl 3-methoxy-2-[2'-(1"-(4"'-bromophenyl)-1"-methyl)-iminooxymethyl]-phenylacrylate (No. 593, Table I)

2.37 g (10 mmol) of methyl 3-methoxy-2-(2'-aminooxymethyl)-phenylacrylate, 1.99 g (10 mmol) of 4-bromoacetophenone, 2 ml of water, 0.8 g of pyridine and 10 ml of methanol are combined and the mixture is stirred for 24 hours at room temperature. The mixture is evaporated down, the residue is partitioned between water/methyl tert-butyl ether and the organic phase is washed with 2N HCl and washed neutral with NaHCO₃ and evaporated down, and the residue is chromatographed over SiO₂ using methyl tert-butyl ether/hexane. 2.1 g (51% of theory) of crystals of melting point 105°-107° C. result.

¹ H-NMR (CDCl₃ : δ=2.22 (s, 3H); 3.70 (s, 3H); 3.80 (s, 3H); 5.15 (s, 2H); 7.16 (dbr, 1H); 7.33 (m, 2H); 7.45 (m, 5H); 7.58 (s, 1H)

EXAMPLE 5 Methyl 2-methoximino-2-[2'-(1"-(4"'-nitrophenyl)-1"-methyl)-iminooxymethyl]-phenylacetate (No. 614, Table II)

2.38 g (10 mmol) of methyl 2-methoximino-2-(2'-aminooxymethyl)-phenylacetate, 1.65 g (10 mmol) of 4-nitroacetophenone, 2 ml of water, 0.8 g of pyridine and 10 ml of methanol are reacted as in Example 4. 2.1 g (55% of theory) of crystals of melting point 87°-89° C. are obtained.

¹ H-NMR (CDCl₃ : δ=2.22 (s, 3H); 3.81 (s, 3H); 4.02 (s, 3H); 5.18 (s, 2H); 7.20 (dd, 1H); 7.4 (m, 3H); 7.75 (dd, 2H); 8.18 (dd, 2H).

EXAMPLE 6 Methyl 3-methoxy-2-[2'-(1"-(4"'-chlorophenyl)-iminooxymethyl]-phenylacrylate (No. 95 Table 5)

a) 5.5 g (15 retool) of methyl 3-methoxy-2-[2'-(phthalimidooxy)-methyl]-phenylacrylate (from Method 4) in 100 ml of methanol are initially taken, and 0.75 g (15 mmol) of hydrazinc hydrate is added at room temperature. After 15 minutes at this temperature, the mixture is evaporated down, the residue is triturated with methyl tert-butyl ether and the cleavage product is filtered off under suction. The mother liquor is evaporated down, the residue is taken up with 50 ml of methanol and 2.1 g (15 mmol) of 4-chlorobenzaldehyde in 50 ml of methanol plus 1 drop of pyridine are added dropwise.

Stirring was carried out overnight at 23° C., after which the product was filtered off under suction, washed with methanol and dried.

2.9 g (54% of theory) of crystals of melting point 87°-89° C. were obtained.

¹ H-NMR (CDCl₃ : δ=3.66 (s, 3H); 3.80 (s, 3H); 5.13 (s, 2H); 7.17 (m, 1H); 7.35 (m, 4H); 7.50 (me, 3H); 7.60 (s, 1H); 8.06 (s, 1H).

b) 50 ml of methanol are slowly added to 1.3 g (55 mmol) of NaH powder under a nitrogen atmosphere (evolution of hydrogen). 7.8 g (50 mmol) of 4-chlorobenzaldehyde oxime in 50 ml of methanol are then added at room temperature. Stirring is carried out for half an hour, after which 14.3 g (50 mmol) of methyl 3-methoxy-2-(2'-bromomethyl)-phenylacrylate in 50 ml of methanol are added dropwise and stirring is carried out at room temperature for a further 48 hours. The white residue is filtered off under suction, washed with methanol and dried. 1.9 g (11% of theory) of a product of melting point 82°-84° C. are obtained.

EXAMPLE 7 Methyl 2-methoximino-2-(2'-phthalimidooxymethy])-pheny]acetate (No. 1, Table 8)

2.0 g (7 mmol) of methyl 2-methoxyimino-2-(2'-bromomethyl)-phenylacetate, 1.1 g (7 mmol) of hydroxyphthalimide and 0.8 g (7.7 mmol) of triethylamine are dissolved in 10 ml of N-methylpyrrolidone and the mixture is stirred for 2 hours at 70° C. Ice water is added and the crystals are filtered off under suction, washed with water and methyl left-buryl ether and dried. There remain 1.5 g (58% of theory) of crystals of melting point 152°-155° C. 1H-NMR (CDCl₃): δ=3.83 (s, 3H); 3.98 (S, 3H); 5.07 (s, 2H); 7.15 (dbr, 1H); 7.45 (mc, 2H); 7.60-7.85 (m, 5H).

The compounds listed in Tables I-IX can be prepared in a similar manner.

                                      TABLE I                                      __________________________________________________________________________      ##STR13##                                                                     No.                                                                               R.sup.3     R.sup.4           Data                                          __________________________________________________________________________     1  Cl          Phenyl                                                          2  Cl          Cyano                                                           3  Cl          Ethoxycarbonyl                                                  4  Cl          Cyclopropyl                                                     5  CF.sub.3    CF.sub.3                                                        6  CF.sub.3    Phenyl                                                          7  CCl.sub.3   CCl.sub.3                                                       8  CCl.sub.3   Phenyl                                                          9  CH.sub.2 Cl Phenyl                                                          10 CF.sub.2 CF.sub.3                                                                          Phenyl                                                          11 CF.sub.2 Cl Phenyl                                                          12 CHCl.sub.2  Phenyl                                                          13 Cyclopropyl Cyclopropyl                                                     14 Cyclopropyl Phenyl            oil; IR (film): 1190,1129,1056,1032,768       15 Cyclopropyl 4-Fluorophenyl    oil; IR (film): 1508,1225,1129,998,839        16 Cyclopropyl 4-Chlorophenyl    oil; IR (film): 1490,1129,1091,1014,1800                                       2                                             17 Cyclopropyl 4-Methoxyphenyl   oil; IR (film): 1251,1177,1129,1033           18 Cyclopropyl 4-Ethoxyphenyl                                                  19 Cyclopropyl 4-Phenoxyphenyl                                                 20 cyclopropyl Pentachlorophenyl                                               21 Cyclopropyl Pentafluorophenyl                                               22 Cyclopentyl Phenyl                                                          23 Cyclohexyl  Phenyl                                                          24 Phenyl      2,2-Dichloro-1-methylcyclopropyl                                25 Phenyl      2,2-Difluorocyclopropyl                                         26 Phenyl      2,2-Dichlorocyclopropyl                                         27 Phenyl      2,2-Dibromocyclopropyl                                          28 Phenyl      2,2,3,3-Tetrafluorocyclobutyl                                   29 Phenyl      2,2-Dimethylcyclopropyl                                         30 Phenyl      1-Methylcyclohexyl                                              31 CN          Methoxymethyl                                                   32 CN          Ethoxymethyl                                                    33 CN          n-Propoxymethyl                                                 34 CN          iso-Propoxymethyl                                               35 CN          tert.-Butoxymethyl                                              36 CN          2-Methoxyprop-2-yl                                                                               oil; IR (film): 1436,1191,1131,1057,1003                                       .                                             37 CN          2-Ethoxyprop-2-yl oil; IR (film): 1191,1177,1131,1095,1010      38 CN          2-n-Propoxyprop-2-yl                                                                             oil; IR (film): 1191,1175,1131,1060,1005      39 CN          2-iso-Propoxyprop-2-yl                                                                           oil; IR (film): 1370,1191,1172,1131,998       40 CN          2-tert.-Butoxyprop-2-yl                                         41 CN          Methylthiomethyl                                                42 CN          tert.-Butylthiomethyl                                           43 CN          2-Methylthioprop-2-yl                                                                            oil; IR (film): 1436,1191,1131,1114,1016,                                      998                                           44 CN          2-iso-Propylthioprop-2-yl                                       45 CN          2-tert.-Butylthioprop-2-yl                                                                       oil; IR (film); 1366,1191,1132,1113,1012,                                      1000                                          46 CN          Methyl                                                          47 CN          Ethyl                                                           48 CN          n-Propyl                                                        49 CN          iso-Propyl        oil; IR (film): 1285,1258,1189,1131,1111,                                      1069,1008                                     50 CN          n-Butyl                                                         51 CN          iso-Butyl                                                       52 CN          sec.-Butyl                                                      53 CN          tert.-Butyl                                                     54 CN          n-Hexyl                                                         55 CN          n-Decyl                                                         56 CN          Cyclopropyl       oil; IR (film): 1207,1190,1130,1057,1003      57 CN          Cyclohexyl                                                      58 CN          Phenylthiomethyl                                                59 CN          2-Phenylthiomethyl                                              60 CN          2-(2'-Chlorophenylthio)prop-2-yl                                61 CN          Ethynyl                                                         62 CN          1-Propynyl                                                      63 CN          Methoxy                                                         64 CN          Ethoxy                                                          65 CN          n-Propoxy                                                       66 CN          iso-Propoxy                                                     67 CN          n-Butoxy                                                        68 CN          iso-Butoxy                                                      69 CN          sec.-Butoxy                                                     70 CN          tert.-Butoxy                                                    71 CN          Methylthio                                                      72 CN          Ethylthio                                                       73 CN          n-Propylthio                                                    74 CN          iso-Propylthio                                                  75 CN          n-Butylthio                                                     76 CN          iso-Butylthio                                                   77 CN          sec.-Butylthio                                                  78 CN          tert.-Butylthio                                                 79 CN          Benzylthio                                                      80 CN          Trifluoromethoxy                                                81 CN          Cyano                                                           82 CN          Amino                                                           83 CN          Methylamino                                                     84 CN          Dimethylamino                                                   85 CN          Ethylamino                                                      86 CN          Diethylamino                                                    87 CN          Di-n-Propylamino                                                88 CN          Di-iso-Propylamino                                              89 CN          Di-n-Butylamino                                                 90 CN          Di-iso-Butylamino                                               91 CN          Acetyl                                                          92 CN          Propion-1-yl                                                    93 CN          Butyr-1-yl                                                      94 CN          iso-Butyr-1-yl                                                  95 CN          Pivaloyl                                                        96 CN          Benzoyl                                                         97 CN          4-Chlorobenzoyl                                                 98 CN          Benzylcarbonyl                                                  99 CN          Methoxycarbonyl                                                 100                                                                               CN          Ethoxycarbonyl                                                  101                                                                               CN          n-Propoxycarbonyl                                               102                                                                               CN          iso-Propoxycarbonyl                                             103                                                                               CN          n-Butoxycarbonyl                                                104                                                                               CN          iso-Butoxycarbonyl                                              105                                                                               CN          sec.-Butoxycarbonyl                                             106                                                                               CN          tert.-Butoxycarbonyl                                            107                                                                               CN          n-Hexoxycarbonyl                                                108                                                                               CN          Phenoxycarbonyl                                                 109                                                                               CN          4-Chlorophenoxycarbonyl                                         110                                                                               CN          Benzyloxycarbonyl                                               111                                                                               CN          Aminocarbonyl                                                   112                                                                               CN          Dimethylaminocarbonyl                                           113                                                                               CN          Diethylaminocarbonyl                                            114                                                                               CN          Di-iso-Propylaminocarbonyl                                      115                                                                               CN          Phenylaminocarbonyl                                             116                                                                               CN          N-Methyl-N-Phenylaminocarbonyl                                  117                                                                               CN          Phenyl            oil; IR (film): 1245,1127,1024,1015,767,7                                      50                                            118                                                                               CN          2-Fluorophenyl                                                  119                                                                               CN          3-Fluorophenyl                                                  120                                                                               CN          4-Fluorophenyl                                                  121                                                                               CN          Pentafluorophenyl                                               122                                                                               CN          2-Chlorophenyl                                                  123                                                                               CN          3-Chlorophenyl                                                  124                                                                               CN          4-Chlorophenyl                                                  125                                                                               CN          Pentachlorophenyl                                               126                                                                               CN          2,3-Dichlorophenyl                                              127                                                                               CN          2,4-Dichlorophenyl                                              128                                                                               CN          2,5-Dichlorophenyl                                              129                                                                               CN          2,6-Dichlorophenyl                                              130                                                                               CN          3,4-Dichlorophenyl                                              131                                                                               CN          3,5-Dichlorophenyl                                              132                                                                               CN          2,3,4-Trichlorophenyl                                           133                                                                               CN          2,3,5-Trichlorophenyl                                           134                                                                               CN          2,3,6-Trichlorophenyl                                           135                                                                               CN          2,4,5-Trichlorophenyl                                           136                                                                               CN          2,4,6-Trichlorophenyl                                           137                                                                               CN          3,4,5-Trichlorophenyl                                           138                                                                               CN          2,3,4,6-Tetrachlorophenyl                                       139                                                                               CN          2,3,5-6-Tetrachlorophenyl                                       140                                                                               CN          2-Bromophenyl                                                   141                                                                               CN          3-Bromophenyl                                                   142                                                                               CN          4-Bromophenyl                                                   143                                                                               CN          2,4-Dibromophenyl                                               144                                                                               CN          3-Bromo-4-fluorophenyl                                          145                                                                               CN          3-Bromo-4-methoxyphenyl                                         146                                                                               CN          2-Iodophenyl                                                    147                                                                               CN          3-Iodophenyl                                                    148                                                                               CN          4-Iodophenyl                                                    149                                                                               CN          2-Chloro-4-fluorophenyl                                         150                                                                               CN          2-Chloro-5-fluorophenyl                                         151                                                                               CN          2-Chloro-6-fluorophenyl                                         152                                                                               CN          2-Chloro-4-bromophenyl                                          153                                                                               CN          2-Bromo-4-chlorophenyl                                          154                                                                               CN          2-Bromo-4-fluorophenyl                                          155                                                                               CN          3-Bromo-4-chlorophenyl                                          156                                                                               CN          3-Chloro-4-fluorophenyl                                         157                                                                               CN          3-Fluoro-4-chlorophenyl                                         158                                                                               CN          2-Cyanophenyl                                                   159                                                                               CN          3-Cyanophenyl                                                   160                                                                               CN          4-Cyanophenyl                                                   161                                                                               CN          2-Nitrophenyl                                                   162                                                                               CN          3-Nitrophenyl                                                   163                                                                               CN          4-Nitrophenyl                                                   164                                                                               CN          2-Methylphenyl                                                  165                                                                               CN          3-Methylphenyl                                                  166                                                                               CN          4-Methylphenyl                                                  167                                                                               CN          2,4-Dimethylphenyl                                              168                                                                               CN          2,6-Dimethylphenyl                                              169                                                                               CN          3,4-Dimethylphenyl                                              170                                                                               CN          3,5-Dimethylphenyl                                              171                                                                               CN          2,3,4-Trimethylphenyl                                           172                                                                               CN          2,3,5-Trimethylphenyl                                           173                                                                               CN          2,3,6-Trimethylphenyl                                           174                                                                               CN          2,4,5-Trimethylphenyl                                           175                                                                               CN          2,4,6-Trimethylphenyl                                           176                                                                               CN          3,4,5-Trimethylphenyl                                           177                                                                               CN          Pentamethylphenyl                                               178                                                                               CN          2-Ethylphenyl                                                   179                                                                               CN          3-Ethylphenyl                                                   180                                                                               CN          4-Ethylphenyl                                                   181                                                                               CN          3,5-Diethylphenyl                                               182                                                                               CN          2-n-Propylphenyl                                                183                                                                               CN          3-n-Propylphenyl                                                184                                                                               CN          4-n-Propylphenyl                                                185                                                                               CN          2-iso-Propylphenyl                                              186                                                                               CN          3-iso-Propylphenyl                                              187                                                                               CN          4-iso-Propylphenyl                                              188                                                                               CN          2,4-Di-iso-Propylphenyl                                         189                                                                               CN          3,5-Di-iso-Propylphenyl                                         190                                                                               CN          4-n-Butylphenyl                                                 191                                                                               CN          4-sec.-Butylphenyl                                              192                                                                               CN          4-iso-Butylphenyl                                               193                                                                               CN          4-tert.-Butylphenyl                                             194                                                                               CN          3-tert.-Butylphenyl                                             195                                                                               CN          2-tert.-Butylphenyl                                             196                                                                               CN          2,4-Di-tert.-Butylphenyl                                        197                                                                               CN          3,5-Di-tert.-Butylphenyl                                        198                                                                               CN          4-n-Hexylphenyl                                                 199                                                                               CN          4-n-Dodecylphenyl                                               200                                                                               CN          2-Methyl-4-tert.-Butylphenyl                                    201                                                                               CN          2-Methyl-6-tert.-Butylphenyl                                    202                                                                               CN          2-Methyl-4-iso-Propylphenyl                                     203                                                                               CN          2-Methyl-4-Cyclohexylphenyl                                     204                                                                               CN          2-Methyl-4-Phenylphenyl                                         205                                                                               CN          2-Methyl-4-Benzylphenyl                                         206                                                                               CN          2-Methyl-4-Phenoxyphenyl                                        207                                                                               CN          2-Methyl-4-Benzyloxyphenyl                                      208                                                                               CN          2-Methyl-3-Chlorophenyl                                         209                                                                               CN          2-Methyl-4-Chlorophenyl                                         210                                                                               CN          2-Methyl-5-Chlorophenyl                                         211                                                                               CN          2-Methyl-6-Chlorophenyl                                         212                                                                               CN          2-Methyl-4-Fluorophenyl                                         213                                                                               CN          2-Methyl-3-Bromophenyl                                          214                                                                               CN          2-Methyl-4-Bromophenyl                                          215                                                                               CN          2-Methyl-3-Methoxyphenyl                                        216                                                                               CN          2-Methyl-4-Methoxyphenyl                                        217                                                                               CN          2-Methyl-5-methoxyphenyl                                        218                                                                               CN          2-Methyl-6-methoxyphenyl                                        219                                                                               CN          2-Methyl-4-iso-Propoxyphenyl                                    220                                                                               CN          2-Methyl-2,5-dimethoxyphenyl                                    221                                                                               CN          2-Methoxyphenyl                                                 222                                                                               CN          3-Methoxyphenyl                                                 223                                                                               CN          4-Methoxyphenyl                                                 224                                                                               CN          2,3-Dimethoxyphenyl                                             225                                                                               CN          2,4-Dimethoxyphenyl                                             226                                                                               CN          2,5-Dimethoxyphenyl                                             227                                                                               CN          2,6-Dimethoxyphenyl                                             228                                                                               CN          3,4-Dimethoxyphenyl                                             229                                                                               CN          3,5-Dimethoxyphenyl                                             230                                                                               CN          3,6-Dimethoxyphenyl                                             231                                                                               CN          2,3,4-Trimethoxyphenyl                                          232                                                                               CN          2,3,5-Trimethoxyphenyl                                          233                                                                               CN          2,3,6-Trimethoxyphenyl                                          234                                                                               CN          2,4,5-Trimethoxyphenyl                                          235                                                                               CN          2,4,6-Trimethoxyphenyl                                          236                                                                               CN          3,4,5-Trimethoxyphenyl                                          237                                                                               CN          2-Ethoxyphenyl                                                  238                                                                               CN          3-Ethoxyphenyl                                                  239                                                                               CN          4-Ethoxyphenyl                                                  240                                                                               CN          2-iso-Propoxyphenyl                                             241                                                                               CN          3-iso-Propoxyphenyl                                             242                                                                               CN          4-iso-Propoxyphenyl                                             243                                                                               CN          3-tert.-Butoxyphenyl                                            244                                                                               CN          4-tert.-Butoxyphenyl                                            245                                                                               CN          2-Trifluoromethoxyphenyl                                        246                                                                               CN          3-Trifluoromethoxyphenyl                                        247                                                                               CN          4-Trifluoromethoxyphenyl                                        248                                                                               CN          3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                         249                                                                               CN          4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                         250                                                                               CN          2-Chloromethylphenyl                                            251                                                                               CN          3-Chloromethylphenyl                                            252                                                                               CN          4-Chloromethylphenyl                                            253                                                                               CN          2-Trifluoromethylphenyl                                         254                                                                               CN          3-Trifluoromethylphenyl                                         255                                                                               CN          4-Trifluoromethylphenyl                                         256                                                                               CN          2-(Methoxyiminomethyl)phenyl                                    257                                                                               CN          3-(Methoxyiminomethyl)phenyl                                    258                                                                               CN          4-(Methoxyiminomethyl)phenyl                                    259                                                                               CN          2-(Ethoxyiminomethyl)phenyl                                     260                                                                               CN          3-(Ethoxylminomethyl)phenyl                                     261                                                                               CN          4-(Ethoxyiminomethyl)phenyl                                     262                                                                               CN          2-(n-Propoxyiminomethyl)phenyl                                  263                                                                               CN          3-(n-Propoxyiminomethyl)phenyl                                  264                                                                               CN          4-(n-Propoxyiminomethyl)phenyl                                  265                                                                               CN          2-(iso-Propoxyiminomethyl)phenyl                                266                                                                               CN          3-(iso-Propoxyiminomethyl)phenyl                                267                                                                               CN          4-(iso-Propoxyiminomethyl)phenyl                                268                                                                               CN          2-(n-Butoxyiminomethyl)phenyl                                   269                                                                               CN          3-(n-Butoxyiminomethyl)phenyl                                   270                                                                               CN          4-(n-Butoxylminomethyl)phenyl                                   271                                                                               CN          2-(iso-Butoxyiminomethyl)phenyl                                 272                                                                               CN          3-(iso-Butoxyiminomethyl)phenyl                                 273                                                                               CN          4-(iso-Butoxyiminomethyl)phenyl                                 274                                                                               CN          2-(tert.-Butoxyiminomethyl)phenyl                               275                                                                               CN          3-(tert.-Butoxyiminomethyl)phenyl                               276                                                                               CN          4-(tert.-Butoxyiminomethyl)phenyl                               277                                                                               CN          2-(n-Pentoxyiminomethyl)phenyl                                  278                                                                               CN          3-(n-Pentoxyiminomethyl)phenyl                                  279                                                                               CN          4-(n-Pentoxyiminomethyl)phenyl                                  280                                                                               CN          2-(n-Hexoxyiminomethyl)phenyl                                   281                                                                               CN          3-(n-Hexoxyiminomethyl)phenyl                                   282                                                                               CN          4-(n-Hexoxyiminomethyl)phenyl                                   283                                                                               CN          2-(Allyloxyiminomethyl)phenyl                                   284                                                                               CN          3-(Allyloxyiminomethyl)phenyl                                   285                                                                               CN          4-(Allyloxyiminomethyl)phenyl                                   286                                                                               CN          2-(Benzyloxyiminomethyl)phenyl                                  287                                                                               CN          3-(Benzyloxyiminomethyl)phenyl                                  288                                                                               CN          4-(Benzyloxyiminomethyi)phenyl                                  289                                                                               CN          2-(Methoxyimino-1'-ethyl)phenyl                                 290                                                                               CN          3-(Methoxyimino-1'-ethyl)phenyl                                 291                                                                               CN          4-(Methoxyimino-1'-ethyl)phenyl                                 292                                                                               CN          2-(Ethoxyimino-1'-ethyi)phenyl                                  293                                                                               CN          3-(Ethoxyimino-1'-ethyl)phenyl                                  294                                                                               CN          4-(Ethoxyimino-1'-ethyl)phenyl                                  295                                                                               CN          2-(n-Propoxyimino-1'-ethyl)phenyl                               296                                                                               CN          3-(n-Propoxyimino-1'-ethyl)phenyl                               297                                                                               CN          4-(n-Propoxyimino-1'-ethyl)phenyl                               298                                                                               CN          2-(n-Butoxyamino-1'-ethyl)phenyl                                299                                                                               CN          3-(n-Butoxyamino-1'-ethyl)phenyl                                300                                                                               CN          4-(n-Butoxyamino-1'-ethyl)phenyl                                301                                                                               CN          2-(n-Pentoxyimino-1'-ethyl)phenyl                               302                                                                               CN          3-(n-Pentoxyimino-1'-ethyl)phenyl                               303                                                                               CN          4-(n-Pentoxyimino-1'-ethyl)phenyl                               304                                                                               CN          2-(n-Hexoxyimino-1'-ethyl)phenyl                                305                                                                               CN          3-(n-Hexoxyimino-1'-ethyl)phenyl                                306                                                                               CN          4-(n-Hexoxyimino-1'-ethyl)phenyl                                307                                                                               CN          2-(Allyloxyimino-1'-ethyl)phenyl                                308                                                                               CN          3-(Allyloxyimino-1'-ethyl)phenyl                                309                                                                               CN          4-(Allyloxyimino-1'-ethyl)phenyl                                310                                                                               CN          2-(Benzyloxyimino-1'-ethyl)phenyl                               311                                                                               CN          3-(Benzyloxyimino-1'-ethyl)phenyl                               312                                                                               CN          4-(Benzyloxyimino-1'-ethyl)phenyl                               313                                                                               CN          2-Phenylphenyl                                                  314                                                                               CN          3-Phenylphenyl                                                  315                                                                               CN          4-Phenylphenyl                                                  316                                                                               CN          2-Phenoxyphenyl                                                 317                                                                               CN          3-Phenoxyphenyl                                                 318                                                                               CN          4-Phenoxyphenyl                                                 319                                                                               CN          2-Benzyloxyphenyl                                               320                                                                               CN          3-Benzyloxyphenyl                                               321                                                                               CN          4-Benzyloxyphenyl                                               322                                                                               CN          4-(Imidazol-1'-yl)phenyl                                        323                                                                               CN          4-(Piperazin-1'-yl)phenyl                                       324                                                                               CN          4-(Morpholin-1'-yl)phenyl                                       325                                                                               CN          4-(Piperidin-1'-yl)phenyl                                       326                                                                               CN          4-(Pyridyl-2'-oxy)phenyl                                        327                                                                               CN          2-Cyclopropylphenyl                                             328                                                                               CN          3-Cyclopropylphenyl                                             329                                                                               CN          4-Cyclopropylphenyl                                             330                                                                               CN          3-Cyclohexylphenyl                                              331                                                                               CN          4-Cyclohexylphenyl                                              332                                                                               CN          4-Oxiranylphenyl                                                333                                                                               CN          4-(1',3'-Dioxan-2'-yl)phenyl                                    334                                                                               CN          4-(Tetrahydropyran-2-yloxy)phenyl                               335                                                                               CN          1-Naphthyl                                                      336                                                                               CN          2-Naphthyl                                                      337                                                                               CN          9-Anthryl                                                       338                                                                               CN          1-Naphtoxy                                                      339                                                                               CN          2-Naphtoxy                                                      340                                                                               CN          9-Anthroxy                                                      341                                                                               CN          Phenoxy                                                         342                                                                               CN          2-Chlorophenoxy                                                 343                                                                               CN          3-Chlorophenoxy                                                 344                                                                               CN          4-Chlorophenoxy                                                 345                                                                               CN          4-Methylphenoxy                                                 346                                                                               CN          4-tert.-Butylphenoxy                                            347                                                                               CN          4-Methoxyphenoxy                                                348                                                                               CN          4-Ethoxyphenoxy                                                 349                                                                               CN          4-tert.-Butoxyphenoxy                                           350                                                                               CN          Phenylthio                                                      351                                                                               CN          2-Chlorophenylthio                                              352                                                                               CN          4-Chlorophenylthio                                              353                                                                               CN          Benzyl                                                          354                                                                               CN          2-Methylbenzyl                                                  355                                                                               CN          3-Methylbenzyl                                                  356                                                                               CN          4-Methylbenzyl                                                  357                                                                               CN          4-tert.-Butylbenzyl                                             358                                                                               CN          2-Chlorobenzyl                                                  359                                                                               CN          3-Chlorobenzyl                                                  360                                                                               CN          4-Chlorobenzyl                                                  361                                                                               CN          2,4-Dichlorobenzyl                                              362                                                                               CN          2,6-Dichlorobenzyl                                              363                                                                               CN          2,4,6-Trichlorobenzyl                                           364                                                                               CN          2-Trifluoromethylbenzyl                                         365                                                                               CN          3-Trifluoromethylbenzyl                                         366                                                                               CN          4-Trifluoromethylbenzyl                                         367                                                                               CN          2-Methoxybenzyl                                                 368                                                                               CN          4-Methoxybenzyl                                                 369                                                                               CN          4-tert.-Butoxybenzyl                                            370                                                                               CN          4-Phenoxybenzyl                                                 371                                                                               CN          1-Phenethyl                                                     372                                                                               CN          2-Phenethyl                                                     373                                                                               CN          1-Phenylpropyl                                                  374                                                                               CN          2-Phenylpropyl                                                  375                                                                               CN          3-Phenylpropyl                                                  376                                                                               CN          2-Methyl-2-phenylpropyl                                         377                                                                               CN          2-Methyl-3-phenylpropyl                                         378                                                                               CN          4-Phenylbutyl                                                   379                                                                               CN          2-Phenyl-1-ethenyl                                              380                                                                               CN          1-Phenyl-1-ethenyl                                              381                                                                               CN          1-Phenyl-1-propenyl                                             382                                                                               CN          1-Phenyl-1-propen-2-yl                                          383                                                                               CN          2,2-Diphenylethenyl                                             384                                                                               CN          Phenoxymethyl                                                   385                                                                               CN          2-Pyridyl                                                       386                                                                               CN          3-Pyridyl                                                       387                                                                               CN          4-Pyridyl                                                       388                                                                               CN          2,6-Pyrimidinyl                                                 389                                                                               CN          1,5-Pyrimidinyl                                                 390                                                                               CN          2-Thienyl                                                       391                                                                               CN          3-Thienyl                                                       392                                                                               CN          2-Furyl                                                         393                                                                               CN          3-Furyl                                                         394                                                                               CN          1-Pyrrolyl                                                      395                                                                               CN          1-Imidazolyl                                                    396                                                                               CN          1,2,4-Triazolyl                                                 397                                                                               CN          1,3,4-Triazolyl                                                 398                                                                               CN          4-Thiazolyl                                                     399                                                                               CN          2-Benzothiazolyl                                                400                                                                               CN          2-Pyridyloxy                                                    401                                                                               CN          2-Pyrimidinyloxy                                                402                                                                               CN          2-Pyridylthio                                                   403                                                                               CN          2-Pyrimidinylthio                                               404                                                                               CN          2-Benzothiazolylthio                                            405                                                                               CN          Phenylthiomethyl                                                406                                                                               CN          2-Pyridylmethyl                                                 407                                                                               CN          3-Pyridylmethyl                                                 408                                                                               CN          Furfuryloxy                                                     409                                                                               CN          Thienylmethoxy                                                  410                                                                               CN          3-Isoxazolylmethoxy                                             411                                                                               CN          2-Oxazolylmethoxy                                               412                                                                               CN          2-Pyridylmethoxy                                                413                                                                               CN          2'-Furyl-2-ethenyl                                              414                                                                               CN          2'-Thienyl-2-ethenyl                                            415                                                                               CN          3'-Pyridyl-2-ethenyl                                            416                                                                               CN          Oxiranyl                                                        417                                                                               CN          1-Aziridinyl                                                    418                                                                               CN          1-Azetidinyl                                                    419                                                                               CN          1-Pyrrolidinyl                                                  420                                                                               CN          2-Tetrahydrofuryl                                               421                                                                               CN          2-Tetrahydropyranyl                                             422                                                                               CN          3-Tetrahydropyranyl                                             423                                                                               CN          1-Piperidinyl                                                   424                                                                               CN          1-Morpholinyl                                                   425                                                                               CN          1-Piperazinyl                                                   426                                                                               CN          1,3-Dioxan-2-yl                                                 427                                                                               CN          3-Tetrahydrothiopyranyl                                         428                                                                               CN          2-Dihydropyranyloxy                                             429                                                                               CN          2-Tetrahydropyranyloxy                                                                           oil; IR (film): 12051131,1087,1047,1004       430                                                                               CN          (CH.sub.2).sub.4                                                431                                                                               CN          (CH.sub.2).sub.5                                                432                                                                               CN          (CH.sub.2).sub.6                                                433                                                                               CN                                                                          434                                                                               CN                                                                          435                                                                               CN                                                                                          ##STR14##                                                      436                                                                               CN                                                                                          ##STR15##                                                      437                                                                               CN                                                                                          ##STR16##                                                      438                                                                               CN                                                                                          ##STR17##                                                      439                                                                               CN                                                                                          ##STR18##                                                      440                                                                               CN                                                                                          ##STR19##                                                      441                                                                               CN          CF.sub.3                                                        442                                                                               CN          2-Fluoroethyl                                                   443                                                                               CN          2,2,2-Trifluoroethyl                                            444                                                                               CN          Pentafluoroethyl                                                445                                                                               CN          Chloromethyl                                                    446                                                                               CN          Dichloromethyl                                                  447                                                                               CN          Trichloromethyl                                                 448                                                                               CN          2-Chloroethyl                                                   449                                                                               CN          2,2,2-Trichloroethyl                                            450                                                                               CN          Pentachloroethyl                                                451                                                                               CN          Cyclopropyl                                                     452                                                                               CN          Cyclobutyl                                                      453                                                                               CN          Cyclopentyl                                                     454                                                                               CN          Cyclohexyl                                                      455                                                                               CN          1-Methylcyclopropyl                                             456                                                                               CN          2,2-Dimethylcyclopropyl                                         457                                                                               CN          1-Methylcyclohexyl                                              458                                                                               CN          2,2-Difluorocyclopropyl                                         459                                                                               CN          2,2-Dichlorocyclopropyl                                         460                                                                               CN          2,2-Dibromocyclopropyl                                          461                                                                               CN          2,2-Dichloro-3-methylcyclopropyl                                462                                                                               CN          2,2,3,3-Tetrafluorocyclobutyl                                   463                                                                               CN          Ethenyl                                                         464                                                                               CN          1-Propenyl                                                      465                                                                               CN          2-methyl-1-propenyl                                             466                                                                               CN          4-Methylpent-3-en-1-yl                                          467                                                                               CN          2-Propenyl                                                      468                                                                               CN          2-Butenyl                                                       469                                                                               CN          1-methyl-2-propenyl                                             470                                                                               CN          3-Methyl-2-butenyl                                              471                                                                               CN          2,2-Difluoroethenyl                                             472                                                                               CN          2,2-Dichloroethenyl                                             473                                                                               CN          3,3,3-Trifluoropropenyl                                         474                                                                               CN          3,3,3-Trichloropropenyl                                         475                                                                               CN          3-Chloro-2-propenyl                                             476                                                                               CN          Cyclopent-1-enyl                                                477                                                                               CN          Cyclopentadienyl                                                478                                                                               CN          Cyclohex-1-enyl                                                 479                                                                               CN          Pentafluorocyclopentadienyl                                     480                                                                               CN          Pentachlorocyclopentadienyl                                     481                                                                               CN          Styryl                                                          482                                                                               CH.sub.3    Methoxymethyl                                                   483                                                                               CH.sub.3    Ethoxymethyl                                                    484                                                                               CH.sub.3    n-Propoxymethyl                                                 485                                                                               CH.sub.3    iso-Propoxymethyl                                               486                                                                               CH.sub.3    tert.-Butoxymethyl                                              487                                                                               CH.sub.3    2-Methoxyprop-2-yl                                              488                                                                               CH.sub.3    2-Ethoxyprop-2-yl                                               489                                                                               CH.sub.3    2-n-Propoxyprop-2-yl                                            490                                                                               CH.sub.3    2-iso-Propoxyprop-2-yl                                          491                                                                               CH.sub.3    2-tert.-Butoxyprop-2-yi                                         492                                                                               CH.sub.3    Methylthiomethyl                                                493                                                                               CH.sub.3    tert.-Butylthiomethyl                                           494                                                                               CH.sub.3    2-Methylthioprop-2-yl                                           495                                                                               CH.sub.3    2-iso-Propylthioprop-2-yl                                       496                                                                               CH.sub.3    2-tert.-Butylthioprop-2-yl                                      497                                                                               CH.sub.3    Methyl                                                          498                                                                               CH.sub.3    Ethyl                                                           499                                                                               CH.sub.3    n-Propyl                                                        500                                                                               CH.sub.3    iso-Propyl                                                      501                                                                               CH.sub.3    n-Butyl                                                         502                                                                               CH.sub.3    iso-Butyl                                                       503                                                                               CH.sub.3    sec.-Butyl                                                      504                                                                               CH.sub.3    tert.-Butyl                                                     505                                                                               CH.sub.3    n-Hexyl                                                         506                                                                               CH.sub.3    n-Decyl                                                         507                                                                               CH.sub.3    Cyclopropyl                                                     508                                                                               CH.sub.3    Cyclohexyl                                                      509                                                                               CH.sub.3    Phenylthiomethyl                                                510                                                                               CH.sub.3    2-Phenylthiomethyl                                              511                                                                               CH.sub.3    2-(2'-Chlorophenylthio)prop-2-yl                                512                                                                               CH.sub.3    Ethynyl                                                         513                                                                               CH.sub.3    1-Propynyl                                                      514                                                                               CH.sub.3    Methoxy                                                         515                                                                               CH.sub.3    Ethoxy                                                          516                                                                               CH.sub.3    n-Propoxy                                                       517                                                                               CH.sub.3    iso-Propoxy                                                     518                                                                               CH.sub.3    n-Butoxy                                                        519                                                                               CH.sub.3    iso-Butoxy                                                      520                                                                               CH.sub.3    sec.-Butoxy                                                     521                                                                               CH.sub.3    tert.-Butoxy                                                    522                                                                               CH.sub.3    Methylthio                                                      523                                                                               CH.sub.3    Ethylthio                                                       524                                                                               CH.sub.3    n-Propylthio                                                    525                                                                               CH.sub.3    iso-Propylthio                                                  526                                                                               CH.sub.3    n-Butylthio                                                     527                                                                               CH.sub.3    iso-Butylthio                                                   528                                                                               CH.sub.3    sec.-Butylthio                                                  529                                                                               CH.sub.3    tert.-Butylthio                                                 530                                                                               CH.sub.3    Benzylthio                                                      531                                                                               CH.sub.3    Trifluoromethoxy                                                532                                                                               CH.sub.3    Cyano                                                           533                                                                               CH.sub.3    Amino                                                           534                                                                               CH.sub.3    Methylamino                                                     535                                                                               CH.sub.3    Dimethylamino                                                   536                                                                               CH.sub.3    Ethylamino                                                      537                                                                               CH.sub.3    Diethylamino                                                    538                                                                               CH.sub.3    Di-n-Propylamino                                                539                                                                               CH.sub.3    Di-iso-Propylamino                                              540                                                                               CH.sub.3    Di-n-Butylamino                                                 541                                                                               CH.sub.3    Di-iso-Butylamino                                               542                                                                               CH.sub.3    Acetyl                                                          543                                                                               CH.sub.3    Propion-1-yl                                                    544                                                                               CH.sub.3    Butyr-1-yl                                                      545                                                                               CH.sub.3    iso-Butyr-1-yl                                                  546                                                                               CH.sub.3    Pivaloyl                                                        547                                                                               CH.sub.3    Benzoyl                                                         548                                                                               CH.sub.3    4-Chlorobenzoyl                                                 549                                                                               CH.sub.3    Benzylcarbonyl                                                  550                                                                               CH.sub.3    Methoxycarbonyl                                                 551                                                                               CH.sub.3    Ethoxycarbonyl                                                  552                                                                               CH.sub.3    n-Propoxycarbonyl                                               553                                                                               CH.sub.3    iso-Propoxycarbonyl                                             554                                                                               CH.sub.3    n-Butoxycarbonyl                                                555                                                                               CH.sub.3    iso-Butoxycarbonyl                                              556                                                                               CH.sub.3    sec.-Butoxycarbonyl                                             557                                                                               CH.sub.3    tert.-Butoxycarbonyl                                            558                                                                               CH.sub.3    n-Hexoxycarbonyl                                                559                                                                               CH.sub.3    Phenoxycarbonyl                                                 560                                                                               CH.sub.3    4-Chlorophenoxycarbonyl                                         561                                                                               CH.sub.3    Benzyloxycarbonyl                                               562                                                                               CH.sub.3    Aminocarbonyl                                                   563                                                                               CH.sub.3    Dimethylaminocarbonyl                                           564                                                                               CH.sub.3    Diethylaminocarbonyl                                            565                                                                               CH.sub.3    Di-iso-Propylaminocarbonyl                                      566                                                                               CH.sub.3    Phenylaminocarbonyl                                             567                                                                               CH.sub.3    N-Methyl-N-Phenylaminocarbonyl                                  568                                                                               CH.sub.3    Phenyl                                                          569                                                                               CH.sub.3    2-Fluorophenyl    oil; IR (film): 1708,1634,1257,1129,761       570                                                                               CH.sub.3    3-Fluorophenyl                                                  571                                                                               CH.sub.3    4-Fluorophenyl    m.p.: 67-68° C.;                                                        IR (KBr): 1691,1629,1295,1253,1132,1037,8                                      48                                            572                                                                               CH.sub.3    Pentafluorophenyl                                               573                                                                               CH.sub.3    2-Chlorophenyl    oil.:                                         574                                                                               CH.sub.3    3-Chlorophenyl                                                  575                                                                               CH.sub.3    4-Chlorophenyl                                                  576                                                                               CH.sub.3    Pentachlorophenyl                                               577                                                                               CH.sub.3    2,3-Dichlorophenyl                                              578                                                                               CH.sub.3    2,4-Dichlorophenyl                                                                               oil; IR (film): 1708,1634,1256,1129           579                                                                               CH.sub.3    2,5-Dichlorophenyl                                                                               m.p.: 80-2° C.;                                                         IR; (KBr): 1704,1634,1250,1132,934,766        580                                                                               CH.sub.3    2,6-Dichlorophenyl                                              581                                                                               CH.sub.3    3,4-Dichlorophenyl                                              582                                                                               CH.sub.3    3,5-Dichlorophenyl                                                                               m.p.: 87-88° C.;                                                        IR (KBr): 1699,1303,1071,1015,932,835         583                                                                               CH.sub.3    2,3,4-Trichlorophenyl                                                                            oil; IR (film): 1709,1627,1257,1131,1109      584                                                                               CH.sub.3    2,3,5-Trichlorophenyl                                           585                                                                               CH.sub.3    2,3,6-Trichlorophenyl                                           586                                                                               CH.sub.3    2,4,5-Trichlorophenyl                                           587                                                                               CH.sub.3    2,4,6-Trichlorophenyl                                           588                                                                               CH.sub.3    3,4,5-Trichlorophenyl                                           589                                                                               CH.sub.3    2,3,4,6-Tetrachlorophenyl                                       590                                                                               CH.sub.3    2,3,5,6-Tetrachlorophenyl                                       591                                                                               CH.sub.3    2-Bromophenyl                                                   592                                                                               CH.sub.3    3-Bromophenyl     m.p.: 60-2° C.;                                                         IR (KBr): 1708,1635,1253,1129,1113,933,77                                      3                                             593                                                                               CH.sub.3    4-Bromophenyl     m.p.: 104-6° C.;                                                        IR (KBr): 1694,1620.1296.1264,1035,938        594                                                                               CH.sub.3    2,4-Dibromophenyl                                               595                                                                               CH.sub.3    3-Bromo-4-Fluorophenyl                                          596                                                                               CH.sub.3    3-Bromo-4-Methoxyphenyl                                         597                                                                               CH.sub.3    2-Iodophenyl                                                    598                                                                               CH.sub.3    3-lodophenyl                                                    599                                                                               CH.sub.3    4-lodophenyl                                                    600                                                                               CH.sub.3    2-Chloro-4-fluorophenyl                                         601                                                                               CH.sub.3    2-Chloro-5-fluorophenyl                                         602                                                                               CH.sub.3    2-Chloro-6-fluorophenyl                                         603                                                                               CH.sub.3    2-Chloro-4-bromophenyl                                          604                                                                               CH.sub.3    2-Bromo-4-chlorophenyl                                          605                                                                               CH.sub.3    2-Bromo-4-fluorophenyl                                          606                                                                               CH.sub.3    3-Bromo-4-chlorophenyl                                          607                                                                               CH.sub.3    3-Chloro-4-fluorophenyl                                         608                                                                               CH.sub.3    3-Fluoro-4-chlorophenyl                                         609                                                                               CH.sub.3    2-Cyanophenyl                                                   610                                                                               CH.sub.3    3-Cyanophenyl                                                   611                                                                               CH.sub.3    4-Cyanophenyl                                                   612                                                                               CH.sub.3    2-Nitrophenyl                                                   613                                                                               CH.sub.3    3-Nitrophenyl                                                   614                                                                               CH.sub.3    4-Nitrophenyl                                                   615                                                                               CH.sub.3    2-Methylphenyl                                                  616                                                                               CH.sub.3    3-Methylphenyl    oil; IR (film): 1709,1634,1256,1129           617                                                                               CH.sub.3    4-Methylphenyl    m.p.: 73-75° C.; IR (KBr):                                              1696,1625,1262,1127,1037,930                  618                                                                               CH.sub.3    2,4-Dimethylphenyl                                              619                                                                               CH.sub.3    2,6-Dimethylphenyl                                              620                                                                               CH.sub.3    3,4-Dimethylphenyl                                              621                                                                               CH.sub.3    3,5-Dimethylphenyl                                              622                                                                               CH.sub.3    2,3,4-Trimethylphenyl                                           623                                                                               CH.sub.3    2,3,5-Trimethylphenyl                                           624                                                                               CH.sub.3    2,3,6-Trimethylphenyl                                           625                                                                               CH.sub.3    2,4,5-Trimethylphenyl                                           626                                                                               CH.sub.3    2,4,6-Trimethylphenyl                                           627                                                                               CH.sub.3    3,4,5-Trimethylpheny)                                           628                                                                               CH.sub.3    Pentamethylphenyl                                               629                                                                               CH.sub.3    2-Ethylphenyl                                                   630                                                                               CH.sub.3    3-Ethylphenyl                                                   631                                                                               CH.sub.3    4-Ethylphenyl                                                   632                                                                               CH.sub.3    3,5-Diethylphenyl                                               633                                                                               CH.sub.3    2-n-Propylphenyl                                                634                                                                               CH.sub.3    3-n-Propylphenyl                                                635                                                                               CH.sub.3    4-n-Propylphenyl                                                636                                                                               CH.sub.3    2-iso-Propylphenyl                                              637                                                                               CH.sub.3    3-iso-Propylphenyl                                              638                                                                               CH.sub.3    4-iso-Propylphenyl                                              639                                                                               CH.sub.3    2,4-Di-iso-Propylphenyl                                         640                                                                               CH.sub.3    3,5-Di-iso-Propylphenyl                                         641                                                                               CH.sub.3    4-n-Butylphenyl                                                 642                                                                               CH.sub.3    4-sec.-Butylphenyl                                              643                                                                               CH.sub.3    4-iso-Butylphenyl                                               644                                                                               CH.sub.3    4-tert.-Butylphenyl                                             645                                                                               CH.sub.3    3-tert.-Butylphenyl                                             646                                                                               CH.sub.3    2-tert.-Butylphenyl                                             647                                                                               CH.sub.3    2,4-Di-tert.-Butylphenyl                                        648                                                                               CH.sub.3    3,5-Di-tert.-Butylphenyl                                        649                                                                               CH.sub.3    4-n-Hexylphenyl                                                 650                                                                               CH.sub.3    4-n-Dodecylphenyl                                               651                                                                               CH.sub.3    2-Methyl-4-tert.-Butylphenyl                                    652                                                                               CH.sub.3    2-Methyl-6-tert.-Butylphenyl                                    653                                                                               CH.sub.3    2-Methyl-4-iso-Propylphenyl                                     654                                                                               CH.sub.3    2-Methyl-4-Cyclohexylphenyl                                     655                                                                               CH.sub.3    2-Methyl-4-Phenylphenyl                                         656                                                                               CH.sub.3    2-Methyl-4-Benzylphenyl                                         657                                                                               CH.sub.3    2-Methyl-4-Phenoxyphenyl                                        658                                                                               CH.sub.3    2-Methyl-4-Benzyloxyphenyl                                      659                                                                               CH.sub.3    2-Methyl-3-Chlorophenyl                                         660                                                                               CH.sub.3    2-Methyl-4-Chlorophenyl                                         661                                                                               CH.sub.3    2-Methyl-5-Chlorophenyl                                         662                                                                               CH.sub.3    2-Methyl-6-Chlorophenyl                                         663                                                                               CH.sub.3    2-Methyl-4-Fluorophenyl                                         664                                                                               CH.sub.3    2-Methyl-3-Bromophenyl                                          665                                                                               CH.sub.3    2-Methyl-4-Bromophenyl                                          666                                                                               CH.sub.3    2-Methyl-3-Methoxyphenyl                                        667                                                                               CH.sub.3    2-Methyl-4-Methoxyphenyl                                        668                                                                               CH.sub.3    2-Methyl-5-Methoxyphenyl                                        669                                                                               CH.sub.3    2-Methyl-6-Methoxyphenyl                                        670                                                                               CH.sub.3    2-Methyl-4-iso-Propoxyphenyl                                    671                                                                               CH.sub.3    2-Methyl-2,5-Dimethoxyphenyl                                    672                                                                               CH.sub.3    2-Methoxyphenyl                                                 673                                                                               CH.sub.3    3-Methoxyphenyl   oil; IR (film): 1708,1634,1285,1256,1129,                                      1111                                          674                                                                               CH.sub.3    4-Methoxyphenyl   oil; IR (film): 1708,1253,1129                675                                                                               CH.sub.3    2,3-Dimethoxyphenyl                                             676                                                                               CH.sub.3    2,4-Dimethoxyphenyl                                             677                                                                               CH.sub.3    2,5-Dimethoxyphenyl                                             678                                                                               CH.sub.3    2,6-Dimethoxyphenyl                                             679                                                                               CH.sub.3    3,4-Dimethoxyphenyl                                             680                                                                               CH.sub.3    3,5-Dimethoxyphenyl                                             681                                                                               CH.sub.3    3,6-Dimethoxyphenyl                                             682                                                                               CH.sub.3    2,3,4-Trimethoxyphenyl                                          683                                                                               CH.sub.3    2,3,5-Trimethoxyphenyl                                          684                                                                               CH.sub.3    2,3,6-Trimethoxyphenyl                                          685                                                                               CH.sub.3    2,4,5-Trimethoxyphenyl                                          686                                                                               CH.sub.3    2,4,6-Trimethoxyphenyl                                          687                                                                               CH.sub.3    3,4,5-Trimethoxyphenyl                                          688                                                                               CH.sub.3    2-Ethoxyphenyl                                                  689                                                                               CH.sub.3    3-Ethoxyphenyl                                                  690                                                                               CH.sub.3    4-Ethoxyphenyl                                                  691                                                                               CH.sub.3    2-iso-Propoxyphenyl                                             692                                                                               CH.sub.3    3-iso-Propoxyphenyl                                             693                                                                               CH.sub.3    4-iso-Propoxyphenyl                                             694                                                                               CH.sub.3    3-tert.-Butoxyphenyl                                            695                                                                               CH.sub.3    4-tert.-Butoxyphenyl                                            696                                                                               CH.sub.3    2-Trifluoromethoxyphenyl                                        697                                                                               CH.sub.3    3-Trifluoromethoxyphenyl                                        698                                                                               CH.sub.3    4-Trifluoromethoxyphenyl                                        699                                                                               CH.sub.3    3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                         700                                                                               CH.sub.3    4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                         701                                                                               CH.sub.3    2-Chloromethylphenyl                                            702                                                                               CH.sub.3    3-Chloromethylphenyl                                            703                                                                               CH.sub.3    4-Chloromethylphenyl                                            704                                                                               CH.sub.3    2-Trifluoromethylphenyl                                                                          oil; IR (film): 1705,1634,1313,1130,1107,                                      767                                           705                                                                               CH.sub.3    3-Trifluoromethylphenyl                                                                          oil; IR (film): 1710,1635,1276,1128           706                                                                               CH.sub.3    4-Trifluoromethylphenyl                                                                          m.p.: 104-5° C.; IR (KBr):                                              1697,1628,1323,1123                           707                                                                               CH.sub.3    2-(Methoxyiminomethyl)phenyl                                    708                                                                               CH.sub.3    3-(Methoxyiminomethyl)phenyl                                    709                                                                               CH.sub.3    4-(Methoxyiminomethyl)phenyl                                    710                                                                               CH.sub.3    2-(Ethoxyiminomethyl)phenyl                                     711                                                                               CH.sub.3    3-(Ethoxyiminomethyl)phenyl                                     712                                                                               CH.sub.3    4-(Ethoxyiminomethyl)phenyl                                     713                                                                               CH.sub.3    2-(n-Propoxyiminomethyl)phenyl                                  714                                                                               CH.sub.3    3-(n-Propoxyiminomethyl)phenyl                                  715                                                                               CH.sub.3    4-(n-Propoxyiminomethyl)phenyl                                  716                                                                               CH.sub.3    2-(iso-Propoxyiminomethyl)phenyl                                717                                                                               CH.sub.3    3-(iso-Propoxyiminomethyl)phenyl                                718                                                                               CH.sub.3    4-(iso-Propoxyiminomethyl)phenyl                                719                                                                               CH.sub.3    2-(n-Butoxyiminomethyl)phenyl                                   720                                                                               CH.sub.3    3-(n-Butoxyiminomethyl)phenyl                                   721                                                                               CH.sub.3    4-(n-Butoxyiminomethyl)phenyl                                   722                                                                               CH.sub.3    2-(iso-Butoxyiminomethyl)phenyl                                 723                                                                               CH.sub.3    3-(iso-Butoxyiminomethyl)phenyl                                 724                                                                               CH.sub.3    4-(iso-Butoxyiminomethyl)phenyl                                 725                                                                               CH.sub.3    2-(tert.-Butoxyiminomethyl)phenyl                               726                                                                               CH.sub.3    3-(tert.-Butoxyiminomethyl)phenyl                               727                                                                               CH.sub.3    4-(tert.-Butoxyiminomethyl)phenyl                               728                                                                               CH.sub.3    2-(n-Pentoxyiminomethyl)phenyl                                  729                                                                               CH.sub. 3   3-(n-Pentoxyiminomethyl)phenyl                                  730                                                                               CH.sub.3    4-(n-Pentoxyiminomethyl)phenyl                                  731                                                                               CH.sub.3    2-(n-Hexoxyiminomethyl)phenyl                                   732                                                                               CH.sub.3    3-(n-Hexoxyiminomethyl)phenyl                                   733                                                                               CH.sub.3    4-(n-Hexoxyiminomethyl)phenyl                                   734                                                                               CH.sub.3    2-(Allyloxyiminomethyl)phenyl                                   735                                                                               CH.sub.3    3-(Allyloxyiminomethyl)phenyl                                   736                                                                               CH.sub.3    4-(Allyloxyiminomethyl)phenyl                                   737                                                                               CH.sub.3    2-(Benzyloxyiminomethyl)phenyl                                  738                                                                               CH.sub.3    3-(Benzyloxyiminomethyl)phenyl                                  739                                                                               CH.sub.3    4-(Benzyloxyiminomethyl)phenyl                                  740                                                                               CH.sub.3    2-(Methoxyimino-1'-ethyl)phenyl                                 741                                                                               CH.sub.3    3-(Methoxyimino-1'-ethyl)phenyl                                 742                                                                               CH.sub.3    4-(Methoxyimino-1'-ethyl)phenyl                                 743                                                                               CH.sub.3    2-(Ethoxyimino-1'-ethyl)phenyl                                  744                                                                               CH.sub.3    3-(Ethoxyimino-1'-ethyl)phenyl                                  745                                                                               CH.sub.3    4-(Ethoxyimino-1'-ethyl)phenyl                                  746                                                                               CH.sub.3    2-(n-Propoxyimino-1'-ethyl)phenyl                               747                                                                               CH.sub.3    3-(n-Propoxyimino-1'-ethyl)phenyl                               748                                                                               CH.sub.3    4-(n-Propoxyimino-1'-ethyl)phenyl                               749                                                                               CH.sub.3    2-(n-Butoxyamino-1'-ethyl)phenyl                                750                                                                               CH.sub.3    3-(n-eutoxyamino-1'-ethyl)phenyl                                751                                                                               CH.sub.3    4-(n-Butoxyamino-1'-ethyl)phenyl                                752                                                                               CH.sub.3    2-(n-Pentoxyimino-1'-ethyl)phenyl                               753                                                                               CH.sub.3    3-(n-Pentoxyimino-1'-ethyl)phenyl                               754                                                                               CH.sub.3    4-(n-Pentoxyimino-1'-ethyl)phenyl                               755                                                                               CH.sub.3    2-(n-Hexoxyimino-1'-ethyl)phenyl                                756                                                                               CH.sub.3    3-(n-Hexoxyimino-1'-ethyl)phenyl                                757                                                                               CH.sub.3    4-(n-Hexoxyimino-1'-ethyl)phenyl                                758                                                                               CH.sub.3    2-(Allyloxyimino-1'-ethyl)phenyl                                759                                                                               CH.sub.3    3-(Allyloxyimino-1'-ethyl)phenyl                                760                                                                               CH.sub.3    4-(Allyloxyimino-1'-ethyl)phenyl                                761                                                                               CH.sub.3    2-(Benzyloxyimino-1'-ethyl)phenyl                               762                                                                               CH.sub.3    3-(Benzyloxyimino-1'-ethyl)phenyl                               763                                                                               CH.sub.3    4-(Benzyloxyimino-1'-ethyl)phenyl                               764                                                                               CH.sub.3    2-Phenylphenyl                                                  765                                                                               CH.sub.3    3-Phenylphenyl                                                  766                                                                               CH.sub.3    4-Phenylphenyl                                                  767                                                                               CH.sub.3    2-Phenoxyphenyl                                                 768                                                                               CH.sub.3    3-Phenoxyphenyl                                                 769                                                                               CH.sub.3    4-Phenoxyphenyl   oil; IR (film): 1708,1489,1240,1129           770                                                                               CH.sub.3    2-Benzyloxyphenyl                                               771                                                                               CH.sub.3    3-Benzyloxyphenyl                                               772                                                                               CH.sub.3    4-Benzyloxyphenyl                                               773                                                                               CH.sub.3    4-(Imidazol-1'-yl)phenyl                                        774                                                                               CH.sub.3    4-(Piperazin-1'-yl)phenyl                                       775                                                                               CH.sub.3    4-(Morpholin-1'-yl)phenyl                                       776                                                                               CH.sub.3    4-(Piperidin-1'-yl)phenyl                                       777                                                                               CH.sub.3    4-(Pyridyl-2'-oxy)phenyl                                        778                                                                               CH.sub.3    2-Cyclopropylphenyl                                             779                                                                               CH.sub.3    3-Cyclopropylphenyl                                             780                                                                               CH.sub.3    4-Cyclopropylphenyl                                             781                                                                               CH.sub.3    3-Cyclohexylphenyl                                              782                                                                               CH.sub.3    4-Cyclohexylphenyl                                              783                                                                               CH.sub.3    4-Oxiranylphenyl                                                784                                                                               CH.sub.3    4-(1',3'-Dioxan-2'-yl)phenyl                                    785                                                                               CH.sub.3    4-(Tetrahydropyran-2-yloxy)phenyl                               786                                                                               CH.sub.3    1-Naphthyl                                                      787                                                                               CH.sub.3    2-Naphthyl                                                      788                                                                               CH.sub.3    9-Anthryl                                                       789                                                                               CH.sub.3    1-Naphthoxy                                                     790                                                                               CH.sub.3    2-Naphthoxy                                                     791                                                                               CH.sub.3    9-Anthroxy                                                      792                                                                               CH.sub.3    Phenoxy                                                         793                                                                               CH.sub.3    2-Chlorophenoxy                                                 794                                                                               CH.sub.3    3-Chlorophenoxy                                                 795                                                                               CH.sub.3    4-Chlorophenoxy                                                 796                                                                               CH.sub.3    4-Methylphenoxy                                                 797                                                                               CH.sub.3    4-tert.-Butylphenoxy                                            798                                                                               CH.sub.3    4-Methoxyphenoxy                                                799                                                                               CH.sub.3    4-Ethoxyphenoxy                                                 800                                                                               CH.sub.3    4-tert.-Butoxyphenoxy                                           801                                                                               CH.sub.3    Phenylthio                                                      802                                                                               CH.sub.3    2-Chlorophenylthio                                              803                                                                               CH.sub.3    4-Chlorophenylthio                                              804                                                                               CH.sub.3    Benzyl                                                          805                                                                               CH.sub.3    2-Methylbenzyl                                                  806                                                                               CH.sub.3    3-Methylbenzyl                                                  807                                                                               CH.sub.3    4-Methylbenyzl                                                  808                                                                               CH.sub.3    4-tert.-Butylbenzyl                                             809                                                                               CH.sub.3    2-Chlorobenzyl                                                  810                                                                               CH.sub.3    3-Chlorobenzyl                                                  811                                                                               CH.sub.3    4-Chlorobenzyl                                                  812                                                                               CH.sub.3    2,4-Dichlorobenzyl                                              813                                                                               CH.sub.3    2,6-Dichlorobenzyl                                              814                                                                               CH.sub.3    2,4,6-Trichlorobenzyl                                           815                                                                               CH.sub.3    2-Trifluoromethylbenzyl                                         816                                                                               CH.sub.3    3-Trifluoromethylbenzyl                                         817                                                                               CH.sub.3    4-Trifluoromethylbenzyl                                         818                                                                               CH.sub.3    2-Methoxybenzyl                                                 819                                                                               CH.sub.3    4-Methoxybenzyl                                                 820                                                                               CH.sub.3    4-tert.-Butoxybenzyl                                            821                                                                               CH.sub.3    4-Phenoxybenzyl                                                 822                                                                               CH.sub.3    1-Phenethyl                                                     823                                                                               CH.sub.3    2-Phenethyl                                                     824                                                                               CH.sub.3    1-Phenylpropyl                                                  825                                                                               CH.sub.3    2-Phenylpropyl                                                  826                                                                               CH.sub.3    3-Phenylpropyl                                                  827                                                                               CH.sub.3    2-Methyl-2-phenylpropyl                                         828                                                                               CH.sub.3    2-Methyl-3-phenylpropyl                                         829                                                                               CH.sub.3    4-Phenylbutyl                                                   830                                                                               CH.sub.3    2-Phenyl-1-ethenyl                                              831                                                                               CH.sub.3    1-Phenyl-1-ethenyl                                              832                                                                               CH.sub.3    1-Phenyl-1-propenyl                                             833                                                                               CH.sub.3    1-Phenyl-1-propen-2-yl                                          834                                                                               CH.sub.3    2,2-Diphenylethenyl                                             835                                                                               CH.sub.3    Phenoxymethyl                                                   836                                                                               CH.sub.3    2-Pyridyl                                                       837                                                                               CH.sub.3    3-Pyridyl                                                       838                                                                               CH.sub.3    4-Pyridyl                                                       839                                                                               CH.sub.3    2,6-Pyrimidinyl                                                 840                                                                               CH.sub.3    1,5-Pyrimidinyl                                                 841                                                                               CH.sub.3    2-Thienyl                                                       842                                                                               CH.sub.3    3-Thienyl                                                       843                                                                               CH.sub.3    2-Furyl                                                         844                                                                               CH.sub.3    3-Furyl                                                         845                                                                               CH.sub.3    1-Pyrrolyl                                                      846                                                                               CH.sub.3    1-imidazolyl                                                    847                                                                               CH.sub.3    1,2,4-Triazolyl                                                 848                                                                               CH.sub.3    1,3,4-Triazolyl                                                 849                                                                               CH.sub.3    4-Thiazolyl                                                     850                                                                               CH.sub.3    2-Benzothiazolyl                                                851                                                                               CH.sub.3    2-Pyridyloxy                                                    852                                                                               CH.sub.3    2-Pyrimidinyloxy                                                853                                                                               CH.sub.3    2-Pyridylthio                                                   854                                                                               CH.sub.3    2-Pyrimidinylthio                                               855                                                                               CH.sub.3    2-Benzothiazolylthio                                            856                                                                               CH.sub.3    Phenylthiomethyl                                                857                                                                               CH.sub.3    2-Pyridylmethyl                                                 858                                                                               CH.sub.3    3-Pyridylmethyl                                                 859                                                                               CH.sub.3    Furfuryloxy                                                     860                                                                               CH.sub.3    Thienylmethoxy                                                  861                                                                               CH.sub.3    3-Isoxazolylmethoxy                                             862                                                                               CH.sub.3    2-Oxazolylmethoxy                                               863                                                                               CH.sub.3    2-Pyridylmethoxy                                                864                                                                               CH.sub.3    2'-Furyl-2-ethenyl                                              865                                                                               CH.sub.3    2'-Thienyl-2-ethenyl                                            866                                                                               CH.sub.3    3'-Pyridyl-2-ethenyl                                            867                                                                               CH.sub.3    Oxiranyl                                                        868                                                                               CH.sub.3    1-Azirldinyl                                                    869                                                                               CH.sub.3    1-Azetidinyl                                                    870                                                                               CH.sub.3    1-Pyrrolidinyl                                                  871                                                                               CH.sub.3    2-Tetrahydrofuryl                                               872                                                                               CH.sub.3    2-Tetrahydropyranyl                                             873                                                                               CH.sub.3    3-Tetrahydropyranyl                                             874                                                                               CH.sub.3    1-Piperidinyl                                                   875                                                                               CH.sub.3    1-Morpholinyl                                                   876                                                                               CH.sub.3    1-Piperazinyl                                                   877                                                                               CH.sub.3    1,3-Dioxan-2-yl                                                 878                                                                               CH.sub.3    3-Tetrahydrothlopyranyl                                         879                                                                               CH.sub.3    2-Dihydropyranyloxy                                             880                                                                               CH.sub.3    2-Tetrahydropyranyloxy                                          881                                                                               CH.sub.3    CF.sub.3                                                        882                                                                               CH.sub.3    2-Fluoroethyl                                                   883                                                                               CH.sub.3    2,2,2-Trifluoroethyl                                            884                                                                               CH.sub.3    Pentafluoroethyl                                                885                                                                               CH.sub.3    Chloromethyl                                                    886                                                                               CH.sub.3    Dichloromethyl                                                  887                                                                               CH.sub.3    Trichloromethyl                                                 888                                                                               CH.sub.3    2-Chloroethyl                                                   889                                                                               CH.sub.3    2,2,2-Trichloroethyl                                            890                                                                               CH.sub.3    Pentachloroethyl                                                891                                                                               CH.sub.3    Cyclopropyl                                                     892                                                                               CH.sub.3    Cyclobutyl                                                      893                                                                               CH.sub.3    Cyclopentyl                                                     894                                                                               CH.sub.3    Cyclohexyl                                                      895                                                                               CH.sub.3    1-Methylcyclopropyl                                             896                                                                               CH.sub.3    2,2-Dimethylcyclopropyl                                         897                                                                               CH.sub.3    1-Methylcyclohexyl                                              898                                                                               CH.sub.3    2,2-Difluorocyclopropyl                                         899                                                                               CH.sub.3    2,2-Dichlorocyclopropyl                                         900                                                                               CH.sub.3    2,2-Dibromocyclopropyl                                          901                                                                               CH.sub.3    2,2-Dichloro-3-methylcyclopropyl                                902                                                                               CH.sub.3    2,2,3,3-Tetrafluorocyclobutyl                                   903                                                                               CH.sub.3    Ethenyl                                                         904                                                                               CH.sub.3    1-Propenyl                                                      905                                                                               CH.sub.3    2-Methyl-1-propenyl                                             906                                                                               CH.sub.3    4-Methylpent-3-en-1-yl                                          907                                                                               CH.sub.3    2-Propenyl                                                      908                                                                               CH.sub.3    2-Butenyl                                                       909                                                                               CH.sub.3    1-Methyl-2-propenyl                                             910                                                                               CH.sub.3    3-Methyl-2-butenyl                                              911                                                                               CH.sub.3    2,2-Difluoroethenyl                                             912                                                                               CH.sub.3    2,2-Dichloroethenyl                                             913                                                                               CH.sub.3    3,3,3-Trifluoropropenyl                                         914                                                                               CH.sub.3    3,3,3-Trichloropropenyl                                         915                                                                               CH.sub.3    3-Chloro-2-propenyl                                             916                                                                               CH.sub.3    Cyclopent-1-enyl                                                917                                                                               CH.sub.3    Cyclopentadienyl                                                918                                                                               CH.sub.3    Cyclohex-1-enyl                                                 919                                                                               CH.sub.3    Pentafluorocyclopentadienyl                                     920                                                                               CH.sub.3    Pentachlorocyclopentadienyl                                     921                                                                               Phenyl      Phenyl                                                          922                                                                               Phenyl      2-Fluorophenyl                                                  923                                                                               Phenyl      4-Fluorophenyl                                                  924                                                                               Phenyl      2-Chlorophenyl                                                  925                                                                               Phenyl      3-Chlorophenyl                                                  926                                                                               Phenyl      4-Chlorophenyl                                                  927                                                                               Phenyl      3,4-Dichlorophenyl                                              928                                                                               Phenyl      4-Nitrophenyl                                                   929                                                                               Phenyl      2-CF.sub.3 -Phenyl                                              930                                                                               Phenyl      3-CF.sub.3 -Phenyl                                              931                                                                               Phenyl      4-CF.sub.3 -Phenyl                                              932                                                                               Phenyl      2-Methylphenyl                                                  933                                                                               Phenyl      3-Methylphenyl                                                  934                                                                               Phenyl      4-Methylphenyl                                                  935                                                                               Phenyl      2,4-Dimethylphenyl                                              936                                                                               Phenyl      4-tert.-Butylphenyl                                             937                                                                               Phenyl      4-Methoxyphenyl                                                 938                                                                               4-Fluorophenyl                                                                             4-Fluorophenyl                                                  939                                                                               2-Fluorophenyl                                                                             4-Fluorophenyl                                                  940                                                                               2-Chlorophenyl                                                                             4-Fluorophenyl                                                  941                                                                               2-Chlorophenyl                                                                             2-Chlorophenyl                                                  942                                                                               3-Chlorophenyl                                                                             3-Chlorophenyl                                                  943                                                                               4-Chlorophenyl                                                                             4-Chlorophenyl                                                  944                                                                               2-Chlorophenyl                                                                             4-Chlorophenyl                                                  945                                                                               4-Methoxyphenyl                                                                            4-Methoxyphenyl                                                 946                                                                               4-Dimethylaminophenyl                                                                      4-Dimethylaminophenyl                                           947                                                                               Phenyl      Naphthyl                                                        948                                                                               Ethyl       Ethyl                                                           949                                                                               Ethyl       n-Propyl                                                        950                                                                               Ethyl       iso-Propyl                                                      951                                                                               Ethyl       n-Butyl                                                         952                                                                               Ethyl       iso-Butyl                                                       953                                                                               Ethyl       2-Methyl-butyl                                                  954                                                                               Ethyl       Benzyl                                                          955                                                                               n-Propyl    n-Propyl                                                        956                                                                               iso-Propyl  iso-Propyl                                                      957                                                                               n-Butyl     n-Butyl                                                         958                                                                               iso-Butyl   iso-Butyl                                                       959                                                                               tert.-Butyl tert.-Butyl                                                     960                                                                               Benzyl      Benzyl                                                          961                                                                               Pentachloroethyl                                                                           Pentachloroethyl                                                962                                                                               n-Hexyl     n-Hexyl                                                         963                                                                               Ethoxycarbonyl                                                                             Ethoxycarbonyl                                                  964                                                                               Phenyl      Benzoyl                                                         965                                                                               Ethyl       Phenyl                                                          966                                                                               n-Butyl     Phenyl                                                          967                                                                               Styryl      Styryl                                                          968                                                                               2-Pyridyl   2-Pyridyl                                                       969                                                                               3-Pyridyl   3-Pyridyl                                                       970                                                                               CH.sub.3    3,5-Dibenzyloxyphenyl                                                                            IR (film): 1707,1581,1256,1157,1129           __________________________________________________________________________

                                      TABLE II                                     __________________________________________________________________________      ##STR20##                                                                     No.                                                                               R.sup.3       R.sup.4           Data                                        __________________________________________________________________________     1  Cl            Phenyl                                                        2  Cl            Cyano                                                         3  Cl            Ethoxycarbonyl                                                4  Cl            Cyclopropyl                                                   5  CF.sub.3      CF.sub.3                                                      6  CF.sub.3      Phenyl                                                        7  CCl.sub.3     CCl.sub.3                                                     8  CCl.sub.3     Phenyl                                                        9  CH.sub.2 Cl   Phenyl                                                        10 CF.sub.2 CF.sub.3                                                                            Phenyl                                                        11 CF.sub.2 Cl   Phenyl                                                        12 CHCl.sub.2    Phenyl                                                        13 Cyclopropyl   Cyclopropyl                                                   14 Cyclopropyl   Phenyl            oil; IR (film): 1437, 1321, 1219,                                              1045, 983, 766                              15 Cyclopropyl   4-Fluorophenyl    oil; IR (film): 1508, 1321, 1222,                                              1046, 985, 839                              16 Cyclopropyl   4-Chlorophenyl    oil; IR (film): 1489, 1321, 1218,                                              1090, 1046, 829                             17 Cyclopropyl   4-Methoxyphenyl   oil; IR (film): 1300, 1250, 1218, 983,                                         833                                         18 Cyclopropyl   4-Ethoxyphenyl                                                19 Cyclopropyl   4-Phenoxyphenyl                                               20 Cyclopropyl   Pentachlorophenyl                                             21 Cyclopropyl   Pentafluorophenyl                                             22 Cyclopentyl   Phenyl                                                        23 Cyclohexyl    Phenyl                                                        24 Phenyl        2,2-Dichloro-1-methylcyclopropyl                              25 Phenyl        2,2-Difluorocyclopropyl                                       26 Phenyl        2,2-Dichlorocyclopropyl                                       27 Phenyl        2,2-Dibromocyclopropyl                                        28 Phenyl        2,2,3,3-Tetrafluorocyclobutyl                                 29 Phenyl        2,2-Dimethylcyclopropyl                                       30 Phenyl        1-Methylcyclohexyl                                            31 CN            Methoxymethyl                                                 32 CN            Ethoxymethyl                                                  33 CN            n-Propoxymethyl                                               34 CN            iso-Propoxymethyl                                             35 CN            tert.-Butoxymethyl                                            36 CN            2-Methoxyprop-2-yl                                                                               m.p.: 83° C.;                                                           IR (KBr): 1437, 1223, 1206, 1069,                                              1006                                        37 CN            2-Ethoxyprop-2-yl oil; IR (film): 1439, 3122, 1221,                                              1202, 1048                                  38 CN            2-n-Propoxyprop-2-yl                                                                             oil; IR (film): 1438, 1322, 1221,                                              1203, 1048                                  39 CN            2-iso-Propoxyprop-2-yl                                                                           m.p.: 74-5° C.                                                          IR (KBr): 1302, 1231, 1169, 1108,                                              1079, 997, 757                              40 CN            2-tert.-Butoxyprop-2-yl                                       41 CN            Methylthiomethyl                                              42 CN            tert.-Butylthiomethyl                                         43 CN            2-Methylthioprop-2-yl                                                                            m.p.: 107° C.;                                                          IR (KBr); 1434, 1297, 1126, 1066,                                              1010, 769                                   44 CN            2-iso-Propylthioprop-2-yl                                                                        oil; IR (film): 1438, 1366, 1321,                                              1221, 1202                                  45 CN            2-tert.-Butylthioprop-2-yl                                    46 CN            Methyl                                                        47 CN            Ethyl                                                         48 CN            n-Propyl                                                      49 CN            iso-Propyl        oil; IR (film): 1439, 1321, 1222,                                              1012, 767                                   50 CN            n-Butyl                                                       51 CN            iso-Butyl                                                     52 CN            sec.-Butyl                                                    53 CN            tert.-Butyl                                                   54 CN            n-Hexyl                                                       55 CN            n-Decyl                                                       56 CN            Cyclopropyl       m.p.: 74-75° C.; IR (KBr):                                              1433, 1223, 1043, 763                       57 CN            Cyclohexyl                                                    58 CN            Phenylthiomethyl                                              59 CN            2-Phenylthiomethyl                                            60 CN            2-(2'-Chlorophenylthio)prop-2-yl                              61 CN            Ethynyl                                                       62 CN            1-Propynyl                                                    63 CN            Methoxy                                                       64 CN            Ethoxy                                                        65 CN            n-Propoxy                                                     66 CN            iso-Propoxy                                                   67 CN            n-Butoxy                                                      68 CN            iso-Butoxy                                                    69 CN            sec.-Butoxy                                                   70 CN            tert.-Butoxy                                                  71 CN            Methylthio                                                    72 CN            Ethylthio                                                     73 CN            n-Propylthio                                                  74 CN            iso-Propylthio                                                75 CN            n-Butylthio                                                   76 CN            iso-Butylthio                                                 77 CN            sec.-Butylthio                                                78 CN            tert.-Butylthio                                               79 CN            Benzylthio                                                    80 CN            Trifluoromethoxy                                              81 CN            Cyano                                                         82 CN            Amino                                                         83 CN            Methylamino                                                   84 CN            Dimethylamino                                                 85 CN            Ethylamino                                                    86 CN            Diethylamino                                                  87 CN            Di-n-Propylamino                                              88 CN            Di-iso-Propylamino                                            89 CN            Di-n-Butylamino                                               90 CN            Di-iso-Butylamino                                             91 CN            Acetyl                                                        92 CN            Propion-1-yl                                                  93 CN            Butyr-1-yl                                                    94 CN            iso-Butyr-1-yl                                                95 CN            Pivaloyl                                                      96 CN            Benzoyl                                                       97 CN            4-Chlorobenzoyl                                               98 CN            Benzylcarbonyl                                                99 CN            Methoxycarbonyl                                               100                                                                               CN            Ethoxycarbonyl                                                101                                                                               CN            n-Propoxycarbonyl                                             102                                                                               CN            iso-Propoxycarbonyl                                           103                                                                               CN            n-Butoxycarbonyl                                              104                                                                               CN            iso-Butoxycarbonyl                                            105                                                                               CN            sec.-Butoxycarbonyl                                           106                                                                               CN            tert.-Butoxycarbonyl                                          107                                                                               CN            n-Hexoxycarbonyl                                              108                                                                               CN            Phenoxycarbonyl                                               109                                                                               CN            4-Chlorophenoxycarbonyl                                       110                                                                               CN            Benzyloxycarbonyl                                             111                                                                               CN            Aminocarbonyl                                                 112                                                                               CN            Dimethylaminocarbonyl                                         113                                                                               CN            Diethylaminocarbonyl                                          114                                                                               CN            Di-iso-Propylaminocarbonyl                                    115                                                                               CN            Phenylaminocarbonyl                                           116                                                                               CN            N-Methyl-N-Phenylaminocarbonyl                                117                                                                               CN            Phenyl            m.p.: 99-100° C.;                                                       IR (KBr): 1436, 1215, 1208, 1097,                                              1026, 944, 766, 690                         118                                                                               CN            2-Fluorophenyl                                                119                                                                               CN            3-Fluorophenyl                                                120                                                                               CN            4-Fluorophenyl                                                121                                                                               CN            Pentafluorophenyl                                             122                                                                               CN            2-Chlorophenyl                                                123                                                                               CN            3-Chlorophenyl                                                124                                                                               CN            4-Chlorophenyl                                                125                                                                               CN            Pentachlorophenyl                                             126                                                                               CN            2,3-Dichlorophenyl                                            127                                                                               CN            2,4-Dichlorophenyl                                            128                                                                               CN            2,5-Dichlorophenyl                                            129                                                                               CN            2,6-Dichlorophenyl                                            130                                                                               CN            3,4-Dichlorophenyl                                            131                                                                               CN            3,5-Dichlorophenyl                                            132                                                                               CN            2,3,4-Trichlorophenyl                                         133                                                                               CN            2,3,5-Trichlorophenyl                                         134                                                                               CN            2,3,6-Trichlorophenyl                                         135                                                                               CN            2,4,5-Trichlorophenyl                                         136                                                                               CN            2,4,6-Trichlorophenyl                                         137                                                                               CN            3,4,5-Trichlorophenyl                                         138                                                                               CN            2,3,4,6-Tetrachlorophenyl                                     139                                                                               CN            2,3,5-6-Tetrachlorophenyl                                     140                                                                               CN            2-Bromophenyl                                                 141                                                                               CN            3-Bromophenyl                                                 142                                                                               CN            4-Bromophenyl                                                 143                                                                               CN            2,4-Dibromophenyl                                             144                                                                               CN            3-Bromo-4-fluorophenyl                                        145                                                                               CN            3-Bromo-4-methoxyphenyl                                       146                                                                               CN            2-Iodophenyl                                                  147                                                                               CN            3-Iodophenyl                                                  148                                                                               CN            4-Iodophenyl                                                  149                                                                               CN            2-Chloro-4-fluorophenyl                                       150                                                                               CN            2-Chloro-5-fluorophenyl                                       151                                                                               CN            2-Chloro-6-fluorophenyl                                       152                                                                               CN            2-Chloro-4-bromophenyl                                        153                                                                               CN            2-Bromo-4-chlorophenyl                                        154                                                                               CN            2-Bromo-4-fluorophenyl                                        155                                                                               CN            3-Bromo-4-chlorophenyl                                        156                                                                               CN            3-Chloro-4-fluorophenyl                                       157                                                                               CN            3-Fluoro-4-chlorophenyl                                       158                                                                               CN            2-Cyanophenyl                                                 159                                                                               CN            3-Cyanophenyl                                                 160                                                                               CN            4-Cyanophenyl                                                 161                                                                               CN            2-Nitrophenyl                                                 162                                                                               CN            3-Nitrophenyl                                                 163                                                                               CN            4-Nitrophenyl                                                 164                                                                               CN            2-Methylphenyl                                                165                                                                               CN            3-Methylphenyl                                                166                                                                               CN            4-Methylphenyl                                                167                                                                               CN            2,4-Dimethylphenyl                                            168                                                                               CN            2,6-Dimethylphenyl                                            169                                                                               CN            3,4-Dimethylphenyl                                            170                                                                               CN            3,5-Dimethylphenyl                                            171                                                                               CN            2,3,4-Trimethylphenyl                                         172                                                                               CN            2,3,5-Trimethylphenyl                                         173                                                                               CN            2,3,6-Trimethylphenyl                                         174                                                                               CN            2,4,5-Trimethylphenyl                                         175                                                                               CN            2,4,6-Trimethylphenyl                                         176                                                                               CN            3,4,5-Trimethylphenyl                                         177                                                                               CN            Pentamethylphenyl                                             178                                                                               CN            2-Ethylphenyl                                                 179                                                                               CN            3-Ethylphenyl                                                 180                                                                               CN            4-Ethylphenyl                                                 181                                                                               CN            3,5-Diethylphenyl                                             182                                                                               CN            2-n-Propylphenyl                                              183                                                                               CN            3-n-Propylphenyl                                              184                                                                               CN            4-n-Propylphenyl                                              185                                                                               CN            2-iso-Propylphenyl                                            186                                                                               CN            3-iso-Propylphenyl                                            187                                                                               CN            4-iso-Propylphenyl                                            188                                                                               CN            2,4-Di-iso-Propylphenyl                                       189                                                                               CN            3,5-Di-iso-Propylphenyl                                       190                                                                               CN            4-n-Butylphenyl                                               191                                                                               CN            4-sec.-Butylphenyl                                            192                                                                               CN            4-iso-Butylphenyl                                             193                                                                               CN            4-tert.-Butylphenyl                                           194                                                                               CN            3-tert.-Butylphenyl                                           195                                                                               CN            2-tert.-Butylphenyl                                           196                                                                               CN            2,4-Di-tert.-Butylphenyl                                      197                                                                               CN            3,5-Di-tert.-Butylphenyl                                      198                                                                               CN            4-n-Hexylphenyl                                               199                                                                               CN            4-n-Dodecylphenyl                                             200                                                                               CN            2-Methyl-4-tert.-Butylphenyl                                  201                                                                               CN            2-Methyl-6-tert.-Butylphenyl                                  202                                                                               CN            2-Methyl-4-iso-Propylphenyl                                   203                                                                               CN            2-Methyl-4-Cyclohexylphenyl                                   204                                                                               CN            2-Methyl-4-Phenylphenyl                                       205                                                                               CN            2-Methyl-4-Benzylphenyl                                       206                                                                               CN            2-Methyl-4-Phenoxyphenyl                                      207                                                                               CN            2-Methyl-4-Benzyloxyphenyl                                    208                                                                               CN            2-Methyl-3-Chlorophenyl                                       209                                                                               CN            2-Methyl-4-Chlorophenyl                                       210                                                                               CN            2-Methyl-5-Chlorophenyl                                       211                                                                               CN            2-Methyl-6-Chlorophenyl                                       212                                                                               CN            2-Methyl-4-Fluorophenyl                                       213                                                                               CN            2-Methyl-3-Bromophenyl                                        214                                                                               CN            2-Methyl-4-Bromophenyl                                        215                                                                               CN            2-Methyl-3-Methoxyphenyl                                      216                                                                               CN            2-Methyl-4-Methoxyphenyl                                      217                                                                               CN            2-Methyl-5-Methoxyphenyl                                      218                                                                               CN            2-Methyl-6-Methoxyphenyl                                      219                                                                               CN            2-Methyl-4-iso-Propoxyphenyl                                  220                                                                               CN            2-Methyl-2,5-Dimethoxyphenyl                                  221                                                                               CN            2-Methoxyphenyl                                               222                                                                               CN            3-Methoxyphenyl                                               223                                                                               CN            4-Methoxyphenyl                                               224                                                                               CN            2,3-Dimethoxyphenyl                                           225                                                                               CN            2,4-Dimethoxyphenyl                                           226                                                                               CN            2,5-Dimethoxyphenyl                                           227                                                                               CN            2,6-Dimethoxyphenyl                                           228                                                                               CN            3,4-Dimethoxyphenyl                                           229                                                                               CN            3,5-Dimethoxyphenyl                                           230                                                                               CN            3,6-Dimethoxyphenyl                                           231                                                                               CN            2,3,4-Trimethoxyphenyl                                        232                                                                               CN            2,3,5-Trimethoxyphenyl                                        233                                                                               CN            2,3,6-Trimethoxyphenyl                                        234                                                                               CN            2,4,5-Trimethoxyphenyl                                        235                                                                               CN            2,4,6-Trimethoxyphenyl                                        236                                                                               CN            3,4,5-Trimethoxyphenyl                                        237                                                                               CN            2-Ethoxyphenyl                                                238                                                                               CN            3-Ethoxyphenyl                                                239                                                                               CN            4-Ethoxyphenyl                                                240                                                                               CN            2-iso-Propoxyphenyl                                           241                                                                               CN            3-iso-Propoxyphenyl                                           242                                                                               CN            4-iso-Propoxyphenyl                                           243                                                                               CN            3-tert.-Butoxyphenyl                                          244                                                                               CN            4-tert.-Butoxyphenyl                                          245                                                                               CN            2-Trifluoromethoxyphenyl                                      246                                                                               CN            3-Trifluoromethoxyphenyl                                      247                                                                               CN            4-Trifluoromethoxyphenyl                                      248                                                                               CN            3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                       249                                                                               CN            4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                       250                                                                               CN            2-Chloromethylphenyl                                          251                                                                               CN            3-Chloromethylphenyl                                          252                                                                               CN            4-Chloromethylphenyl                                          253                                                                               CN            2-Trifluoromethylphenyl                                       254                                                                               CN            3-Trifluoromethylphenyl                                       255                                                                               CN            4-Trifluoromethylphenyl                                       256                                                                               CN            2-(Methoxyiminomethyl)phenyl                                  257                                                                               CN            3-(Methoxyiminomethyl)phenyl                                  258                                                                               CN            4-(Methoxyiminomethyl)phenyl                                  259                                                                               CN            2-(Ethoxyiminomethyl)phenyl                                   260                                                                               CN            3-(Ethoxyiminomethyl)phenyl                                   261                                                                               CN            4-(Ethoxyiminomethyl)phenyl                                   262                                                                               CN            2-(n-Propoxyiminomethyl)phenyl                                263                                                                               CN            3-(n-Propoxyiminomethyl)phenyl                                264                                                                               CN            4-(n-Propoxyiminomethyl)phenyl                                265                                                                               CN            2-(iso-Propoxyiminomethyl)phenyl                              266                                                                               CN            3-(iso-Propoxyiminomethyl)phenyl                              267                                                                               CN            4-(iso-Propoxyiminomethyl)phenyl                              268                                                                               CN            2-(n-Butoxyiminomethyl)phenyl                                 269                                                                               CN            3-(n-Butoxyiminomethyl)phenyl                                 270                                                                               CN            4-(n-Butoxyiminomethyl)phenyl                                 271                                                                               CN            2-(iso-Butoxyiminomethyl)phenyl                               272                                                                               CN            3-(iso-Butoxyiminomethyl)phenyl                               273                                                                               CN            4-(iso-Butoxyiminomethyl)phenyl                               274                                                                               CN            2-(tert.-Butoxyiminomethyl)phenyl                             275                                                                               CN            3-(tert.-Butoxyiminomethyl)phenyl                             276                                                                               CN            4-(tert.-Butoxyiminomethyl)phenyl                             277                                                                               CN            2-(n-Pentoxyiminomethyl)phenyl                                278                                                                               CN            3-(n-Pentoxyiminomethyl)phenyl                                279                                                                               CN            4-(n-Pentoxyiminomethyl)phenyl                                280                                                                               CN            2-(n-Hexoxyiminomethyl)phenyl                                 281                                                                               CN            3-(n-Hexoxyiminomethyl)phenyl                                 282                                                                               CN            4-(n-Hexoxyiminomethyl)phenyl                                 283                                                                               CN            2-(Allyloxyiminomethyl)phenyl                                 284                                                                               CN            3-(Allyloxyiminomethyl)phenyl                                 285                                                                               CN            4-(Allytoxyiminomethyl)phenyl                                 286                                                                               CN            2-(Benzyloxyiminomethyl)phenyl                                287                                                                               CN            3-(Benzyloxyiminomethyl)phenyl                                288                                                                               CN            4-(Benzyloxyiminomethyl)phenyl                                289                                                                               CN            2-(Methoxyimino-1'-ethyl)phenyl                               290                                                                               CN            3-(Methoxyimino-1'-ethyl)phenyl                               291                                                                               CN            4-(Methoxyimino-1'-ethyl)phenyl                               292                                                                               CN            2-(Ethoxyimino-1'-ethyl)phenyl                                293                                                                               CN            3-(Ethoxylmino-1'-ethyl)phenyl                                294                                                                               CN            4-(Ethoxyimino-1'-ethyl)phenyl                                295                                                                               CN            2-(n-Propoxyimino-1'-ethyl)phenyl                             296                                                                               CN            3-(n-Propoxyimino-1'-ethyl)phenyl                             297                                                                               CN            4-(n-Propoxyimino-1'-ethyl)phenyl                             298                                                                               CN            2-(n-Butoxyamino-1'-ethyl)phenyl                              299                                                                               CN            3-(n-Butoxyamino-1'  -ethyl)phenyl                            300                                                                               CN            4-(n-Butoxyamino-1'-ethyl)phenyl                              301                                                                               CN            2-(n-Pentoxyimino-1'-ethyl)phenyl                             302                                                                               CN            3-(n-Pentoxyimino-1'-ethyl)phenyl                             303                                                                               CN            4-(n-Pentoxyimino-1'-ethyl)phenyl                             304                                                                               CN            2-(n-Hexoxyimino-1'-ethyl)phenyl                              305                                                                               CN            3-(n-Hexoxyimino-1'-ethyl)phenyl                              306                                                                               CN            4-(n-Hexoxyimino-1'-ethyl)phenyl                              307                                                                               CN            2-(Allyloxyimino-1'-ethyl)phenyl                              308                                                                               CN            3-(Allyloxyimino-1'-ethyl)phenyl                              309                                                                               CN            4-(Allyloxyimino-1'-ethyl)phenyl                              310                                                                               CN            2-(Benzyloxyimino-1'-ethyl)phenyl                             311                                                                               CN            3-(Benzyloxyimino-1'-ethyl)phenyl                             312                                                                               CN            4-(Benzyloxyimino-1'-ethyl)phenyl                             313                                                                               CN            2-Phenylphenyl                                                314                                                                               CN            3-Phenylphenyl                                                315                                                                               CN            4-Phenylphenyl                                                316                                                                               CN            2-Phenoxyphenyl                                               317                                                                               CN            3-Phenoxyphenyl                                               318                                                                               CN            4-Phenoxyphenyl                                               319                                                                               CN            2-Benzyloxyphenyl                                             320                                                                               CN            3-Benzyloxyphenyl                                             321                                                                               CN            4-Benzyloxyphenyl                                             322                                                                               CN            4-(Imidazol-1'-yl)phenyl                                      323                                                                               CN            4-(Piperazin-1'-yl)phenyl                                     324                                                                               CN            4-(Morpholin-1'-yl)phenyl                                     325                                                                               CN            4-(Piperidin-1'-yl)phenyl                                     326                                                                               CN            4-(Pyridyl-2'-oxy)phenyl                                      327                                                                               CN            2-Cyclopropylphenyl                                           328                                                                               CN            3-Cyclopropylphenyl                                           329                                                                               CN            4-Cyclopropylphenyl                                           330                                                                               CN            3-Cyclohexylphenyl                                            331                                                                               CN            4-Cyclohexylphenyl                                            332                                                                               CN            4-Oxiranylphenyl                                              333                                                                               CN            4-(1',3'-Dioxan-2'-yl)phenyl                                  334                                                                               CN            4-(Tetrahydropyran-2-yloxy)phenyl                             335                                                                               CN            1-Naphthyl                                                    336                                                                               CN            2-Naphthyl                                                    337                                                                               CN            9-Anthryl                                                     338                                                                               CN            1-Naphthoxy                                                   339                                                                               CN            2-Naphthoxy                                                   340                                                                               CN            9-Anthroxy                                                    341                                                                               CN            Phenoxy                                                       342                                                                               CN            2-Chlorophenoxy                                               343                                                                               CN            3-Chlorophenoxy                                               344                                                                               CN            4-Chlorophenoxy                                               345                                                                               CN            4-Methylphenoxy                                               346                                                                               CN            4-tert.-Butylphenoxy                                          347                                                                               CN            4-Methoxyphenoxy                                              348                                                                               CN            4-Ethoxyphenoxy                                               349                                                                               CN            4-tert.-Butoxyphenoxy                                         350                                                                               CN            Phenylthio                                                    351                                                                               CN            2-Chlorophenylthio                                            352                                                                               CN            4-Chlorophenylthio                                            353                                                                               CN            Benzyl                                                        354                                                                               CN            2-Methylbenzyl                                                355                                                                               CN            3-Methylbenzyl                                                356                                                                               CN            4-Methylbenyzl                                                357                                                                               CN            4-tert.-Butylbenzyl                                           358                                                                               CN            2-Chlorobenzyl                                                359                                                                               CN            3-Chlorobenzyl                                                360                                                                               CN            4-Chlorobenzyl                                                361                                                                               CN            2,4-Dichlorobenzyl                                            362                                                                               CN            2,6-Dichlorobenzyl                                            363                                                                               CN            2,4,6-Trichlorobenzyl                                         364                                                                               CN            2-Trifluoromethylbenzyl                                       365                                                                               CN            3-Trifluoromethylbenzyl                                       366                                                                               CN            4-Trifluoromethylbenzyl                                       367                                                                               CN            2-Methoxybenzyl                                               368                                                                               CN            4-Methoxybenzyl                                               369                                                                               CN            4-tert.-Butoxybenzyl                                          370                                                                               CN            4-Phenoxybenzyl                                               371                                                                               CN            1-Phenethyl                                                   372                                                                               CN            2-Phenethyl                                                   373                                                                               CN            1-Phenylpropyl                                                374                                                                               CN            2-Phenylpropyl                                                375                                                                               CN            3-Phenylpropyl                                                376                                                                               CN            2-Methyl-2-phenylpropyl                                       377                                                                               CN            2-Methyl-3-phenylpropyl                                       378                                                                               CN            4-Phenylbutyl                                                 379                                                                               CN            2-Phenyl-1-ethenyl                                            380                                                                               CN            1-Phenyl-1-ethenyl                                            381                                                                               CN            1-Phenyl-1-propenyl                                           382                                                                               CN            1-Phenyl-1-propen-2-yl                                        383                                                                               CN            2,2-Diphenylethenyl                                           384                                                                               CN            Phenoxymethyl                                                 385                                                                               CN            2-Pyridyl                                                     386                                                                               CN            3-Pyridyl                                                     387                                                                               CN            4-Pyridyl                                                     388                                                                               CN            2,6-Pyrimidinyl                                               389                                                                               CN            1,5-Pyrimidinyl                                               390                                                                               CN            2-Thienyl                                                     391                                                                               CN            3-Thienyl                                                     392                                                                               CN            2-Furyl                                                       393                                                                               CN            3-Furyl                                                       394                                                                               CN            1-Pyrrolyl                                                    395                                                                               CN            1-Imidazolyl                                                  396                                                                               CN            1,2,4-Triazolyl                                               397                                                                               CN            1,3,4-Triazolyl                                               398                                                                               CN            4-Thiazolyl                                                   399                                                                               CN            2-Benzothiazolyl                                              400                                                                               CN            2-Pyridyloxy                                                  401                                                                               CN            2-Pyrimidinyloxy                                              402                                                                               CN            2-Pyridylthio                                                 403                                                                               CN            2-Pyrimidinylthio                                             404                                                                               CN            2-Benzothiazolylthio                                          405                                                                               CN            Phenylthiomethyl                                              406                                                                               CN            2-Pyridylmethyl                                               407                                                                               CN            3-Pyridylmethyl                                               408                                                                               CN            Furfuryloxy                                                   409                                                                               CN            Thienylmethoxy                                                410                                                                               CN            3-Isoxazolylmethoxy                                           411                                                                               CN            2-Oxazolylmethoxy                                             412                                                                               CN            2-Pyridylmethoxy                                              413                                                                               CN            2'-Furyl-2-ethenyl                                            414                                                                               CN            2'-Thienyl-2-ethenyl                                          415                                                                               CN            3'-Pyridyl-2-ethenyl                                          416                                                                               CN            Oxiranyl                                                      417                                                                               CN            1-Aziridinyl                                                  418                                                                               CN            1-Azetidinyl                                                  419                                                                               CN            1-Pyrrolidinyl                                                420                                                                               CN            2-Tetrahydrofuryl                                             421                                                                               CN            2-Tetrahydropyranyl                                           422                                                                               CN            3-Tetrahydropyranyl                                           423                                                                               CN            1-Piperidinyl                                                 424                                                                               CN            1-Morpholinyl                                                 425                                                                               CN            1-Piperazinyl                                                 426                                                                               CN            1,3-Dioxan-2-yl                                               427                                                                               CN            3-Tetrahydrothiopyranyl                                       428                                                                               CN            2-Dihydropyranyloxy                                           429                                                                               CN            2-Tetrahydropyranyloxy                                                                           oil; IR (film): 1439, 1228, 1209,                                              1050, 1025 767                              430                                                                               CN            (CH.sub.2).sub.4                                              431                                                                               CN            (CH.sub.2).sub.5                                              432                                                                               CN            (CH.sub.2).sub.6                                              433                                                                               CN                                                                          434                                                                               CN                                                                          435                                                                               CN                                                                                            ##STR21##                                                    436                                                                               CN                                                                                            ##STR22##                                                    437                                                                               CN                                                                                            ##STR23##                                                    438                                                                               CN                                                                                            ##STR24##                                                    439                                                                               CN                                                                                            ##STR25##                                                    440                                                                               CN                                                                                            ##STR26##                                                    441                                                                               CN            CF.sub.3                                                      442                                                                               CN            2-Fluoroethyl                                                 443                                                                               CN            2,2,2-Trifluoroethyl                                          444                                                                               CN            Pentafluoroethyl                                              445                                                                               CN            Chloromethyl                                                  446                                                                               CN            Dichloromethyl                                                447                                                                               CN            Trichloromethyl                                               448                                                                               CN            2-Chloroethyl                                                 449                                                                               CN            2,2,2-Trichloroethyl                                          450                                                                               CN            Pentachloroethyl                                              451                                                                               CN            Cyclopropyl                                                   452                                                                               CN            Cyclobutyl                                                    453                                                                               CN            Cyclopentyl                                                   454                                                                               CN            Cyclohexyl                                                    455                                                                               CN            1-Methylcyclopropyl                                           456                                                                               CN            2,2-Dimethylcyclopropyl                                       457                                                                               CN            1-Methylcyclohexyl                                            458                                                                               CN            2,2-Difluorocyclopropyl                                       459                                                                               CN            2,2-Dichlorocyclopropyl                                       460                                                                               CN            2,2-Dibromocyclopropyl                                        461                                                                               CN            2,2-Dichloro-3-Methylcyclopropyl                              462                                                                               CN            2,2,3,3-Tetrafluorocyclobutyl                                 463                                                                               CN            Ethenyl                                                       464                                                                               CN            1-Propenyl                                                    465                                                                               CN            2-Methyl-1-propenyl                                           466                                                                               CN            4-Methylpent-3-en-1-yl                                        467                                                                               CN            2-Propenyl                                                    468                                                                               CN            2-Butenyl                                                     469                                                                               CN            1-Methyl-2-propenyl                                           470                                                                               CN            3-Methyl-2-butenyl                                            471                                                                               CN            2,2-Difluoroethenyl                                           472                                                                               CN            2,2-Dichloroethenyl                                           473                                                                               CN            3,3,3-Trifluoropropenyl                                       474                                                                               CN            3,3,3-Trichloropropenyl                                       475                                                                               CN            3-Chloro-2-propenyl                                           476                                                                               CN            Cyclopent-1-enyl                                              477                                                                               CN            Cyclopentadienyl                                              478                                                                               CN            Cyclohex-1-enyl                                               479                                                                               CN            Pentafluorocyclopentadienyl                                   480                                                                               CN            Pentachlorocyclopentadienyl                                   481                                                                               CN            Styryl                                                        482                                                                               CH.sub.3      Methoxymethyl                                                 483                                                                               CH.sub.3      Ethoxymethyl                                                  484                                                                               CH.sub.3      n-Propoxymethyl                                               485                                                                               CH.sub.3      iso-Propoxymethyl                                             486                                                                               CH.sub.3      tert.-Butoxymethyl                                            487                                                                               CH.sub.3      2-Methoxyprop-2-yl                                            488                                                                               CH.sub.3      2-Ethoxyprop-2-yl                                             489                                                                               CH.sub.3      2-n-Propoxyprop-2-yl                                          490                                                                               CH.sub.3      2-iso-Propoxyprop-2-yl                                        491                                                                               CH.sub.3      2-tert.-Butoxyprop-2-yl                                       492                                                                               CH.sub.3      Methylthiomethyl                                              493                                                                               CH.sub.3      tert.-Butylthiomethyl                                         494                                                                               CH.sub.3      2-Methylthioprop-2-yl                                         495                                                                               CH.sub.3      2-iso-Propylthioprop-2-yl                                     496                                                                               CH.sub.3      2-tert.-Butylthioprop-2-yl                                    497                                                                               CH.sub.3      Methyl            m.p. 68-71°  C.; IR (KBr):                                              1137, 1298, 1067, 1023, 1007, 771           498                                                                               CH.sub.3      Ethyl                                                         499                                                                               CH.sub.3      n-Propyl                                                      500                                                                               CH.sub.3      iso-Propyl                                                    501                                                                               CH.sub.3      n-Butyl                                                       502                                                                               CH.sub.3      iso-Butyl                                                     503                                                                               CH.sub.3      sec.-Butyl                                                    504                                                                               CH.sub.3      tert.-Butyl                                                   505                                                                               CH.sub.3      n-Hexyl                                                       506                                                                               CH.sub.3      n-Decyl                                                       507                                                                               CH.sub.3      Cyclopropyl                                                   508                                                                               CH.sub.3      Cyclohexyl                                                    509                                                                               CH.sub.3      Phenylthiomethyl                                              510                                                                               CH.sub.3      2-Phenylthiomethyl                                            511                                                                               CH.sub.3      2-(2'-Chlorophenylthio)prop-2-yl                              512                                                                               CH.sub.3      Ethynyl                                                       513                                                                               CH.sub.3      1-Propynyl                                                    514                                                                               CH.sub.3      Methoxy                                                       515                                                                               CH.sub.3      Ethoxy                                                        516                                                                               CH.sub.3      n-Propoxy                                                     517                                                                               CH.sub.3      iso-Propoxy                                                   518                                                                               CH.sub.3      n-Butoxy                                                      519                                                                               CH.sub.3      iso-Butoxy                                                    520                                                                               CH.sub.3      sec.-Butoxy                                                   521                                                                               CH.sub.3      tert.-Butoxy                                                  522                                                                               CH.sub.3      Methylthio                                                    523                                                                               CH.sub.3      Ethylthio                                                     524                                                                               CH.sub.3      n-Propylthio                                                  525                                                                               CH.sub.3      iso-Propylthio                                                526                                                                               CH.sub.3      n-Butylthio                                                   527                                                                               CH.sub.3      iso-Butylthio                                                 528                                                                               CH.sub.3      sec.-Butylthio                                                529                                                                               CH.sub.3      tert.-Butylthio                                               530                                                                               CH.sub.3      Benzylthio                                                    531                                                                               CH.sub.3      Trifluoromethoxy                                              532                                                                               CH.sub.3      Cyano                                                         533                                                                               CH.sub.3      Amino                                                         534                                                                               CH.sub.3      Methylamino                                                   535                                                                               CH.sub.3      Dimethylamino                                                 536                                                                               CH.sub.3      Ethylamino                                                    537                                                                               CH.sub.3      Diethylamino                                                  538                                                                               CH.sub.3      Di-n-Propylamino                                              539                                                                               CH.sub.3      Di-iso-Propylamino                                            540                                                                               CH.sub.3      Di-n-Butylamino                                               541                                                                               CH.sub.3      Di-iso-Butylamino                                             542                                                                               CH.sub.3      Acetyl                                                        543                                                                               CH.sub.3      Propion-1-yl                                                  544                                                                               CH.sub.3      Butyr-1-yl                                                    545                                                                               CH.sub. 3     iso-Butyr-1-yl                                                546                                                                               CH.sub.3      Pivaloyl                                                      547                                                                               CH.sub.3      Benzoyl                                                       548                                                                               CH.sub.3      4-Chlorobenzoyl                                               549                                                                               CH.sub.3      Benzylcarbonyl                                                550                                                                               CH.sub.3      Methoxycarbonyl                                               551                                                                               CH.sub.3      Ethoxycarbonyl                                                552                                                                               CH.sub.3      n-Propoxycarbonyl                                             553                                                                               CH.sub.3      iso-Propoxycarbonyl                                           554                                                                               CH.sub.3      n-Butoxycarbonyl                                              555                                                                               CH.sub.3      iso-Butoxycarbonyl                                            556                                                                               CH.sub.3      sec.-Butoxycarbonyl                                           557                                                                               CH.sub.3      tert.-Butoxycarbonyl                                          558                                                                               CH.sub.3      n-Hexoxycarbonyl                                              559                                                                               CH.sub.3      Phenoxycarbonyl                                               560                                                                               CH.sub.3      4-Chlorophenoxycarbonyl                                       561                                                                               CH.sub.3      Benzyloxycarbonyl                                             562                                                                               CH.sub.3      Aminocarbonyl                                                 563                                                                               CH.sub.3      Dimethylaminocarbonyl                                         564                                                                               CH.sub.3      Diethylaminocarbonyl                                          565                                                                               CH.sub.3      Di-iso-Propylaminocarbonyl                                    566                                                                               CH.sub.3      Phenylaminocarbonyl                                           567                                                                               CH.sub.3      N-Methyl-N-Phenylaminocarbonyl                                568                                                                               CH.sub.3      Phenyl                                                        569                                                                               CH.sub.3      2-Fluorophenyl    m.p.: 89-91° C.; IR (KBr):                                              1732, 1071, 1012, 998, 768                  570                                                                               CH.sub.3      3-Fluorophenyl    m.p.: 83-85° C.; IR (KBr):                                              1724, 1204, 1067, 1031, 1015, 955           571                                                                               CH.sub.3      4-Fluorophenyl    m.p.: 76-8° C.;                                                         IR (KBr): 1737, 1510, 1302, 1224,                                              1072, 1031, 1015, 933                       572                                                                               CH.sub.3      Pentafluorophenyl                                             573                                                                               CH.sub.3      2-Chlorophenyl                                                574                                                                               CH.sub.3      3-Chlorophenyl    m.p.: 61-63° C.; IR (KBr):                                              1735, 1070, 1015, 1002, 785                 575                                                                               CH.sub.3      4-Chlorophenyl    oil; IR (film): 1708, 1634, 1256,                                              1129                                        576                                                                               CH.sub.3      Pentachlorophenyl                                             577                                                                               CH.sub.3      2,3-Dichlorophenyl                                            578                                                                               CH.sub.3      2,4-Dichlorophenyl                                            579                                                                               CH.sub.3      2,5-Dichlorophenyl                                            580                                                                               CH.sub.3      2,6-Dichlorophenyl                                            581                                                                               CH.sub.3      3,4-Dichlorophenyl                                            582                                                                               CH.sub.3      3,5-Dichlorophenyl                                                                               m.p.: 95-7° C.;                                                         IR (KBr): 1723, 1556, 1224, 1067,                                              1030, 1014, 957                             583                                                                               CH.sub.3      2,3,4-Trichlorophenyl                                                                            m.p.: 118-20° C.                     584                                                                               CH.sub.3      2,3,5-Trichlorophenyl                                         585                                                                               CH.sub.3      2,3,6-Trichlorophenyl                                         586                                                                               CH.sub.3      2,4,5-Trichlorophenyl                                         587                                                                               CH.sub.3      2,4,6-Trichlorophenyl                                         588                                                                               CH.sub.3      3,4,5-Trichlorophenyl                                         589                                                                               CH.sub.3      2,3,4,6-Tetrachlorophenyl                                     590                                                                               CH.sub.3      2,3,5-6-Tetrachlorophenyl                                     591                                                                               CH.sub.3      2-Bromophenyl                                                 592                                                                               CH.sub.3      3-Bromophenyl     m.p.: 80-4° C.;                                                         IR (KBr): 1723, 1556, 1224, 1067,                                              1030, 1014, 957                             593                                                                               CH.sub.3      4-Bromophenyl     m.p.: 73-75° C.;                                                        IR (KBr): 1736, 1071, 1029, 1015, 932       594                                                                               CH.sub.3      2,4-Dibromophenyl                                             595                                                                               CH.sub.3      3-Bromo-4-fluorophenyl                                        596                                                                               CH.sub.3      3-Bromo-4-methoxyphenyl                                       597                                                                               CH.sub.3      2-Iodophenyl                                                  598                                                                               CH.sub.3      3-Iodophenyl                                                  599                                                                               CH.sub.3      4-Iodophenyl                                                  600                                                                               CH.sub.3      2-Chloro-4-fluorophenyl                                       601                                                                               CH.sub.3      2-Chloro-5-fluorophenyl                                       602                                                                               CH.sub.3      2-Chloro-6-fluorophenyl                                       603                                                                               CH.sub.3      2-Chloro-4-bromophenyl                                        604                                                                               CH.sub.3      2-Bromo-4-chlorophenyl                                        605                                                                               CH.sub.3      2-Bromo-4-fluorophenyl                                        606                                                                               CH.sub.3      3-Bromo-4-chlorophenyl                                        607                                                                               CH.sub.3      3-Chloro-4-fluorophenyl                                       608                                                                               CH.sub.3      3-Fluoro-4-chlorophenyl                                       609                                                                               CH.sub.3      2-Cyanophenyl                                                 610                                                                               CH.sub.3      3-Cyanophenyl                                                 611                                                                               CH.sub.3      4-Cyanophenyl                                                 612                                                                               CH.sub.3      2-Nitrophenyl                                                 613                                                                               CH.sub.3      3-Nitrophenyl                                                 614                                                                               CH.sub.3      4-Nitrophenyl     m.p.: 88-90° C.;                                                        IR (KBr): 1725, 1512, 1342, 1219,                                              1068, 1009, 854                             615                                                                               CH.sub.3      2-Methylphenyl                                                616                                                                               CH.sub.3      3-Methylphenyl    m.p.: 93-96° C.                      617                                                                               CH.sub.3      4-Methylphenyl    m.p.: 82-84° C.; IR (KBr):                                              1722, 1068, 1038, 1015, 920                 618                                                                               CH.sub.3      2,4-Dimethylphenyl                                            619                                                                               CH.sub.3      2,6-Dimethylphenyl                                            620                                                                               CH.sub.3      3,4-Dimethylphenyl                                            621                                                                               CH.sub.3      3,5-Dimethylphenyl                                            622                                                                               CH.sub.3      2,3,4-Trimethylphenyl                                         623                                                                               CH.sub.3      2,3,5-Trimethylphenyl                                         624                                                                               CH.sub.3      2,3,6-Trimethylphenyl                                         625                                                                               CH.sub.3      2,4,5-Trimethylphenyl                                         626                                                                               CH.sub.3      2,4,6-Trimethylphenyl                                         627                                                                               CH.sub.3      3,4,5-Trimethylphenyl                                         628                                                                               CH.sub.3      Pentamethylphenyl                                             629                                                                               CH.sub.3      2-Ethylphenyl                                                 630                                                                               CH.sub.3      3-Ethylphenyl                                                 631                                                                               CH.sub.3      4-Ethylphenyl                                                 632                                                                               CH.sub.3      3,5-Diethylphenyl                                             633                                                                               CH.sub.3      2-n-Propylphenyl                                              634                                                                               CH.sub.3      3-n-Propylphenyl                                              635                                                                               CH.sub.3      4-n-Propylphenyl                                              636                                                                               CH.sub.3      2-iso-Propylphenyl                                            637                                                                               CH.sub.3      3-iso-Propylphenyl                                            638                                                                               CH.sub.3      4-iso-Propylphenyl                                            639                                                                               CH.sub.3      2,4-Di-iso-Propylphenyl                                       640                                                                               CH.sub.3      3,5-Di-iso-Propylphenyl                                       641                                                                               CH.sub.3      4-n-Butylphenyl                                               642                                                                               CH.sub.3      4-sec.-Butylphenyl                                            643                                                                               CH.sub.3      4-iso-Butylphenyl                                             6444                                                                              CH.sub.3      4-tert.-Butylphenyl                                                                              m.p.: 45-50° C.                      645                                                                               CH.sub.3      3-tert.-Butylphenyl                                           646                                                                               CH.sub.3      2-tert.-Butylphenyl                                           647                                                                               CH.sub.3      2,4-Di-tert.-Butylphenyl                                      648                                                                               CH.sub.3      3,5-Di-tert.-Butylphenyl                                      649                                                                               CH.sub.3      4-n-Hexylphenyl                                               650                                                                               CH.sub.3      4-n-Dodecylphenyl                                             651                                                                               CH.sub.3      2-Methyl-4-tert.-Butylphenyl                                  652                                                                               CH.sub.3      2-Methyl-6-tert.-Butylphenyl                                  653                                                                               CH.sub.3      2-Methyl-4-iso-Propylphenyl                                   654                                                                               CH.sub.3      2-Methyl-4-Cyclohexylphenyl                                   655                                                                               CH.sub.3      2-Methyl-4-Phenylphenyl                                       656                                                                               CH.sub.3      2-Methyl-4-Benzylphenyl                                       657                                                                               CH.sub.3      2-Methyl-4-Phenoxyphenyl                                      658                                                                               CH.sub.3      2-Methyl-4-Benzyloxyphenyl                                    659                                                                               CH.sub.3      2-Methyl-3-Chlorophenyl                                       660                                                                               CH.sub.3      2-Methyl-4-Chlorophenyl                                       661                                                                               CH.sub.3      2-Methyl-5-Chlorophenyl                                       662                                                                               CH.sub.3      2-Methyl-6-chlorophenyl                                       663                                                                               CH.sub.3      2-Methyl-4-fluorophenyl                                       664                                                                               CH.sub.3      2-Methyl-3-bromophenyl                                        665                                                                               CH.sub.3      2-Methyl-4-bromophenyl                                        666                                                                               CH.sub.3      2-Methyl-3-methoxyphenyl                                      667                                                                               CH.sub.3      2-Methyl-4-methoxyphenyl                                      668                                                                               CH.sub.3      2-Methyl-5-methoxyphenyl                                      669                                                                               CH.sub.3      2-Methyl-6-methoxyphenyl                                      670                                                                               CH.sub.3      2-Methyl-4-iso-Propoxyphenyl                                  671                                                                               CH.sub.3      2-Methyl-2,5-dimethoxyphenyl                                  672                                                                               CH.sub.3      2-Methoxyphenyl   m.p.: 74-6° C.;                                                         IR (KBr): 1741, 1433, 1295, 1249,                                              1224, 1067, 1022, 878                       673                                                                               CH.sub.3      3-Methoxyphenyl                                               674                                                                               CH.sub.3      4-Methoxyphenyl   m.p.: 89-91° C.                      675                                                                               CH.sub.3      2,3-Dimethoxyphenyl                                           676                                                                               CH.sub.3      2,4-Dimethoxyphenyl                                           677                                                                               CH.sub.3      2,5-Dimethoxyphenyl                                           678                                                                               CH.sub.3      2,6-Dimethoxyphenyl                                           679                                                                               CH.sub.3      3,4-Dimethoxyphenyl                                           680                                                                               CH.sub.3      3,5-Dimethoxyphenyl                                           681                                                                               CH.sub.3      3,6-Dimethoxyphenyl                                           682                                                                               CH.sub.3      2,3,4-Trimethoxyphenyl                                        683                                                                               CH.sub.3      2,3,5-Trimethoxyphenyl                                        684                                                                               CH.sub.3      2,3,6-Trimethoxyphenyl                                        685                                                                               CH.sub.3      2,4,5-Trimethoxyphenyl                                        686                                                                               CH.sub.3      2,4,6-Trimethoxyphenyl                                        687                                                                               CH.sub.3      3,4,5-Trimethoxyphenyl                                        688                                                                               CH.sub.3      2-Ethoxyphenyl                                                689                                                                               CH.sub.3      3-Ethoxyphenyl                                                690                                                                               CH.sub.3      4-Ethoxyphenyl                                                691                                                                               CH.sub.3      2-iso-Propoxyphenyl                                           692                                                                               CH.sub.3      3-iso-Propoxyphenyl                                           693                                                                               CH.sub.3      4-iso-Propoxyphenyl                                           694                                                                               CH.sub.3      3-tert.-Butoxyphenyl                                          695                                                                               CH.sub.3      4-tert.-Butoxyphenyl                                          696                                                                               CH.sub.3      2-Trifluoromethoxyphenyl                                      697                                                                               CH.sub.3      3-Trifluoromethoxyphenyl                                      698                                                                               CH.sub.3      4-Trifluoromethoxyphenyl                                      699                                                                               CH.sub.3      3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                       700                                                                               CH.sub.3      4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                       701                                                                               CH.sub.3      2-Chloromethylphenyl                                          702                                                                               CH.sub.3      3-Chloromethylphenyl                                          703                                                                               CH.sub.3      4-Chloromethylphenyl                                          704                                                                               CH.sub.3      2-Trifluoromethylphenyl                                                                          m.p.: 78-80° C.; IR (KBr):                                              1741, 1315, 1116, 1068, 1010                705                                                                               CH.sub.3      3-Trifluoromethylphenyl                                                                          m.p.: 70-72° C.;                                                        IR (KBr): 1740, 1297, 1281, 1164,                                              1124, 1073, 1010                            706                                                                               CH.sub.3      4-Trifluoromethylphenyl                                                                          m.p.: 57-58° C.; (IR (KBr):                                             1728, 1333, 1318, 1106, 1069, 986           707                                                                               CH.sub.3      2-(Methoxyiminomethyl)phenyl                                  708                                                                               CH.sub.3      3-(Methoxyiminomethyl)phenyl                                  709                                                                               CH.sub.3      4-(Methoxyiminomethyl)phenyl                                  710                                                                               CH.sub.3      2-(Ethoxyiminomethyl)phenyl                                   711                                                                               CH.sub.3      3-(Ethoxyiminomethyl)phenyl                                   712                                                                               CH.sub.3      4-(Ethoxyiminomethyl)phenyl                                   713                                                                               CH.sub.3      2-(n-Propoxyiminomethyl)phenyl                                714                                                                               CH.sub.3      3-(n-Propoxyiminomethyl)phenyl                                715                                                                               CH.sub.3      4-(n-Propoxyiminomethyl)phenyl                                716                                                                               CH.sub.3      2-(iso-Propoxyiminomethyl)phenyl                              717                                                                               CH.sub.3      3-(iso-Propoxyiminomethyl)phenyl                              718                                                                               CH.sub.3      4-(iso-Propoxyiminomethyl)phenyl                              719                                                                               CH.sub.3      2-(n-Butoxyiminomethyl)phenyl                                 720                                                                               CH.sub.3      3-(n-Butoxyiminomethyl)phenyl                                 721                                                                               CH.sub.3      4-(n-Butoxyiminomethyl)phenyl                                 722                                                                               CH.sub.3      2-(iso-Butoxyiminomethyl)phenyl                               723                                                                               CH.sub.3      3-(iso-Butoxyiminomethyl)phenyl                               724                                                                               CH.sub.3      4-(iso-Butoxyiminomethyl)phenyl                               725                                                                               CH.sub.3      2-(tert.-Butoxyiminomethyl)phenyl                             726                                                                               CH.sub.3      3-(tert.-Butoxyiminomethyl)phenyl                             727                                                                               CH.sub.3      4-(tert.-Butoxyiminomethyl)phenyl                             728                                                                               CH.sub.3      2-(n-Pentoxyiminomethyl)phenyl                                729                                                                               CH.sub.3      3-(n-Pentoxyiminomethyl)phenyl                                730                                                                               CH.sub.3      4-(n-Pentoxyiminomethyl)phenyl                                731                                                                               CH.sub.3      2-(n-Hexoxyiminomethyl)phenyl                                 732                                                                               CH.sub.3      3-(n-Hexoxyiminomethyl)phenyl                                 733                                                                               CH.sub.3      4-(n-Hexoxyiminomethyl)phenyl                                 734                                                                               CH.sub.3      2-(Allyloxyiminomethyl)phenyl                                 735                                                                               CH.sub.3      3-(Allyloxylminomethyl)phenyl                                 736                                                                               CH.sub.3      4-(Allyloxyiminomethyl)phenyl                                 737                                                                               CH.sub.3      2-(Benzyloxyiminomethyl)phenyl                                738                                                                               CH.sub. 3     3-(Benzyloxyiminomethyl)phenyl                                739                                                                               CH.sub.3      4-(Benzyloxyiminomethyl)phenyl                                740                                                                               CH.sub.3      2-(Methoxyimino-1'-ethyl)phenyl                               741                                                                               CH.sub.3      3-(Methoxyimino-1'-ethyl)phenyl                               742                                                                               CH.sub.3      4-(Methoxyimino-1'-ethyl)phenyl                               743                                                                               CH.sub.3      2-(Ethoxyimino-1'-ethyl)phenyl                                744                                                                               CH.sub.3      3-(Ethoxyimino-1'-ethyl)phenyl                                745                                                                               CH.sub.3      4-(Ethoxyimino-1'-ethyl)phenyl                                746                                                                               CH.sub.3      2-(n-Propoxyimino-1'-ethyl)phenyl                             747                                                                               CH.sub.3      3-(n-Propoxyimino-1'-ethyl)phenyl                             748                                                                               CH.sub.3      4-(n-Propoxyimino-1'-ethyl)phenyl                             749                                                                               CH.sub.3      2-(n-Butoxyamino-1'-ethyl)phenyl                              750                                                                               CH.sub.3      3-(n-Butoxyamino-1'-ethyl)phenyl                              751                                                                               CH.sub.3      4-(n-Butoxyamino-1'-ethyl)phenyl                              752                                                                               CH.sub.3      2-(n-Pentoxyimino-1'-ethyl)phenyl                             753                                                                               CH.sub.3      3-(n-Pentoxyimino-1'-ethyl)phenyl                             754                                                                               CH.sub.3      4-(n-Pentoxyimino-1'-ethyl)phenyl                             755                                                                               CH.sub.3      2-(n-Hexoxyimino-1'-ethyl)phenyl                              756                                                                               CH.sub.3      3-(n-Hexoxyimino-1'-ethyl)phenyl                              757                                                                               CH.sub.3      4-(n-Hexoxyimino-1'-ethyl)phenyl                              758                                                                               CH.sub.3      2-(Allyloxyimino-1'-ethyl)phenyl                              759                                                                               CH.sub.3      3-(Allyloxyimino-1'-ethyl)phenyl                              760                                                                               CH.sub.3      4-(Allyloxyimino-1'-ethyl)phenyl                              761                                                                               CH.sub.3      2-(Benzyloxyimino-1'-ethyl)phenyl                             762                                                                               CH.sub.3      3-(Benzyloxyimino-1'-ethyl)phenyl                             763                                                                               CH.sub.3      4-(Benzyloxyimino-1'-ethyl)phenyl                             764                                                                               CH.sub.3      2-Phenylphenyl                                                765                                                                               CH.sub.3      3-Phenylphenyl                                                766                                                                               CH.sub.3      4-Phenylphenyl                                                767                                                                               CH.sub.3      2-Phenoxyphenyl                                               768                                                                               CH.sub.3      3-Phenoxyphenyl                                               769                                                                               CH.sub.3      4-Phenoxyphenyl   m.p.: 91-3° C.;                                                         IR (KBr): 1732, 1587, 1491, 1241,                                              1071, 1014, 995, 769                        770                                                                               CH.sub.3      2-Benzyloxyphenyl                                             771                                                                               CH.sub.3      3-Benzyloxyphenyl                                             772                                                                               CH.sub.3      4-Benzyloxyphenyl                                             773                                                                               CH.sub.3      4-(Imidazol-1'-yl)phenyl                                      774                                                                               CH.sub.3      4-(Piperazin-1'-yl)phenyl                                     775                                                                               CH.sub.3      4-(Morpholin-1'-yl)phenyl                                     776                                                                               CH.sub.3      4-(Piperidin-1'-yl)phenyl                                     777                                                                               CH.sub.3      4-(Pyridyl-2'-oxy)phenyl                                      778                                                                               CH.sub.3      2-Cyclopropylphenyl                                           779                                                                               CH.sub.3      3-Cyclopropylphenyl                                           780                                                                               CH.sub.3      4-Cyclopropylphenyl                                           781                                                                               CH.sub.3      3-Cyclohexylphenyl                                            782                                                                               CH.sub.3      4-Cyclohexylphenyl                                                                               m.p.: 53-5° C.                       783                                                                               CH.sub.3      4-Oxiranylphenyl                                              784                                                                               CH.sub.3      4-(1',3'-Dioxan-2'-yl)phenyl                                  785                                                                               CH.sub.3      4-(Tetrahydropyran-2-yloxy)phenyl                             786                                                                               CH.sub.3      1-Naphthyl                                                    787                                                                               CH.sub.3      2-Naphthyl                                                    788                                                                               CH.sub.3      9-Anthryl                                                     789                                                                               CH.sub.3      1-Naphthoxy                                                   790                                                                               CH.sub.3      2-Naphthoxy                                                   791                                                                               CH.sub.3      9-Anthroxy                                                    792                                                                               CH.sub.3      Phenoxy                                                       793                                                                               CH.sub.3      2-Chlorophenoxy                                               794                                                                               CH.sub.3      3-Chlorophenoxy                                               795                                                                               CH.sub.3      4-Chlorophenoxy                                               796                                                                               CH.sub.3      4-Methylphenoxy                                               797                                                                               CH.sub.3      4-tert.-Butylphenoxy                                          798                                                                               CH.sub.3      4-Methoxyphenoxy                                              799                                                                               CH.sub.3      4-Ethoxyphenoxy                                               800                                                                               CH.sub.3      4-tert.-Butoxyphenoxy                                         801                                                                               CH.sub.3      Phenylthio                                                    802                                                                               CH.sub.3      2-Chlorophenylthio                                            803                                                                               CH.sub.3      4-Chlorophenylthio                                            804                                                                               CH.sub.3      Benzyl                                                        805                                                                               CH.sub.3      2-Methylbenzyl                                                806                                                                               CH.sub.3      3-Methylbenzyl                                                807                                                                               CH.sub.3      4-Methylbenzyl                                                808                                                                               CH.sub.3      4-tert.-Butylbenzyl                                           809                                                                               CH.sub.3      2-Chlorobenzyl                                                810                                                                               CH.sub.3      3-Chlorobenzyl                                                811                                                                               CH.sub.3      4-Chlorobenzyl                                                812                                                                               CH.sub.3      2,4-Dichlorobenzyl                                            813                                                                               CH.sub.3      2,6-Dichlorobenzyl                                            814                                                                               CH.sub.3      2,4,6-Trichlorobenzyl                                         815                                                                               CH.sub.3      2-Trifluoromethylbenzyl                                       816                                                                               CH.sub.3      3-Trifluoromethylbenzyl                                       817                                                                               CH.sub.3      4-Trifluoromethylbenzyl                                       818                                                                               CH.sub.3      2-Methoxybenzyl                                               819                                                                               CH.sub.3      4-Methoxybenzyl                                               820                                                                               CH.sub.3      4-tert.-Butoxybenzyl                                          821                                                                               CH.sub.3      4-Phenoxybenzyl                                               822                                                                               CH.sub.3      1-Phenethyl                                                   823                                                                               CH.sub.3      2-Phenethyl                                                   824                                                                               CH.sub.3      1-Phenylpropyl                                                825                                                                               CH.sub.3      2-Phenylpropyl                                                826                                                                               CH.sub.3      3-Phenylpropyl                                                827                                                                               CH.sub.3      2-Methyl-2-phenylpropyl                                       828                                                                               CH.sub.3      2-Methyl-3-phenylpropyl                                       829                                                                               CH.sub.3      4-Phenylbutyl                                                 830                                                                               CH.sub.3      2-Phenyl-1-ethenyl                                            831                                                                               CH.sub.3      1-Phenyl-1-ethenyl                                            832                                                                               CH.sub.3      1-Phenyl-1-propenyl                                           833                                                                               CH.sub.3      1-Phenyl-1-propen-2-yl                                        834                                                                               CH.sub.3      2,2-Diphenylethenyl                                           835                                                                               CH.sub.3      Phenoxymethyl                                                 836                                                                               CH.sub.3      2-Pyridyl                                                     837                                                                               CH.sub.3      3-Pyridyl                                                     838                                                                               CH.sub.3      4-Pyridyl                                                     839                                                                               CH.sub.3      2,6-Pyrimidinyl                                               840                                                                               CH.sub.3      1,5-Pyrimidinyl                                               841                                                                               CH.sub.3      2-Thienyl                                                     842                                                                               CH.sub.3      3-Thienyl                                                     843                                                                               CH.sub.3      2-Furyl                                                       844                                                                               CH.sub.3      3-Furyl                                                       845                                                                               CH.sub.3      1-Pyrrolyl                                                    846                                                                               CH.sub.3      1-Imidazolyl                                                  847                                                                               CH.sub.3      1,2,4-Triazolyl                                               848                                                                               CH.sub.3      1,3,4-Triazolyl                                               849                                                                               CH.sub.3      4-Thiazolyl                                                   850                                                                               CH.sub.3      2-Benzothiazolyl                                              851                                                                               CH.sub.3      2-Pyridyloxy                                                  852                                                                               CH.sub.3      2-Pyrimidinyloxy                                              853                                                                               CH.sub.3      2-Pyridylthio                                                 854                                                                               CH.sub.3      2-Pyrimidinylthio                                             855                                                                               CH.sub.3      2-Benzothiazolylthio                                          856                                                                               CH.sub.3      Phenylthiomethyl                                              857                                                                               CH.sub.3      2-Pyridylmethyl                                               858                                                                               CH.sub.3      3-Pyridylmethyl                                               859                                                                               CH.sub.3      Furfuryloxy                                                   860                                                                               CH.sub.3      Thienylmethoxy                                                861                                                                               CH.sub.3      3-Isoxazolylmethoxy                                           862                                                                               CH.sub.3      2-Oxazolylmethoxy                                             863                                                                               CH.sub.3      2-Pyridylmethoxy                                              864                                                                               CH.sub.3      2'-Furyl-2-ethenyl                                            865                                                                               CH.sub.3      2'-Thienyl-2-ethenyl                                          866                                                                               CH.sub.3      3'-Pyridyl-2-ethenyl                                          867                                                                               CH.sub.3      Oxiranyl                                                      868                                                                               CH.sub.3      1-Aziridinyl                                                  869                                                                               CH.sub.3      1-Azetidinyl                                                  870                                                                               CH.sub.3      1-Pyrrolidinyl                                                871                                                                               CH.sub.3      2-Tetrahydrofuryl                                             872                                                                               CH.sub.3      2-Tetrahydropyranyl                                           873                                                                               CH.sub.3      3-Tetrahydropyranyl                                           874                                                                               CH.sub.3      1-Piperidinyl                                                 875                                                                               CH.sub.3      1-Morpholinyl                                                 876                                                                               CH.sub.3      1-Piperazinyl                                                 877                                                                               CH.sub.3      1,3-Dioxan-2-yl                                               878                                                                               CH.sub.3      3-Tetrahydrothiopyranyl                                       879                                                                               CH.sub.3      2-Dihydropyranyloxy                                           880                                                                               CH.sub.3      2-Tetrahydropyranyloxy                                        881                                                                               CH.sub.3      CF.sub.3                                                      882                                                                               CH.sub.3      2-Fluoroethyl                                                 883                                                                               CH.sub.3      2,2,2-Trifluoroethyl                                          884                                                                               CH.sub.3      Pentafluoroethyl                                              885                                                                               CH.sub.3      Chloromethyl                                                  886                                                                               CH.sub.3      Dichloromethyl                                                887                                                                               CH.sub.3      Trichloromethyl                                               888                                                                               CH.sub.3      2-Chloroethyl                                                 889                                                                               CH.sub.3      2,2,2-Trichloroethyl                                          890                                                                               CH.sub.3      Pentachloroethyl                                              891                                                                               CH.sub.3      Cyclopropyl                                                   892                                                                               CH.sub.3      Cyclobutyl                                                    893                                                                               CH.sub.3      Cyclopentyl                                                   894                                                                               CH.sub.3      Cyclohexyl                                                    895                                                                               CH.sub.3      1-Methylcyclopropyl                                           896                                                                               CH.sub.3      2,2-Dimethylcyclopropyl                                       897                                                                               CH.sub.3      1-Methylcyclohexyl                                            898                                                                               CH.sub.3      2,2-Difluorocyclopropyl                                       899                                                                               CH.sub.3      2,2-Dichlorocyclopropyl                                       900                                                                               CH.sub.3      2,2-Dibromocyclopropyl                                        901                                                                               CH.sub.3      2,2-Dichloro-3-Methylcyclopropyl                              902                                                                               CH.sub.3      2,2,3,3-Tetrafluorocyclobutyl                                 903                                                                               CH.sub.3      Ethenyl                                                       904                                                                               CH.sub.3      1-Propenyl                                                    905                                                                               CH.sub.3      2-Methyl-1-propenyl                                           906                                                                               CH.sub.3      4-Methylpent-3-en-1-yl                                        907                                                                               CH.sub.3      2-Propenyl                                                    908                                                                               CH.sub.3      2-Butenyl                                                     909                                                                               CH.sub.3      1-Methyl-2-propenyl                                           910                                                                               CH.sub.3      3-Methyl-2-butenyl                                            911                                                                               CH.sub.3      2,2-Difluoroethenyl                                           912                                                                               CH.sub.3      2,2-Dichloroethenyl                                           913                                                                               CH.sub.3      3,3,3-Trifluoropropenyl                                       914                                                                               CH.sub.3      3,3,3-Trichloropropenyl                                       915                                                                               CH.sub.3      3-Chloro-2-propenyl                                           916                                                                               CH.sub.3      Cyclopent-1-enyl                                              917                                                                               CH.sub.3      Cyclopentadienyl                                              918                                                                               CH.sub.3      Cyclohex-1-enyl                                               919                                                                               CH.sub.3      Pentafluorocyclopentadienyl                                   920                                                                               CH.sub.3      Pentachlorocyclopentadienyl                                   921                                                                               Phenyl        Phenyl                                                        922                                                                               Phenyl        2-Fluorophenyl                                                923                                                                               Phenyl        4-Fluorophenyl                                                924                                                                               Phenyl        2-Chlorophenyl                                                925                                                                               Phenyl        3-Chlorophenyl                                                926                                                                               Phenyl        4-Chlorophenyl                                                927                                                                               Phenyl        3,4-Dichlorophenyl                                            928                                                                               Phenyl        4-Nitrophenyl                                                 929                                                                               Phenyl        2-CF.sub.3 -Phenyl                                            930                                                                               Phenyl        3-CF.sub.3 -Phenyl                                            931                                                                               Phenyl        4-CF.sub.3 -Phenyl                                            932                                                                               Phenyl        2-Methylphenyl                                                933                                                                               Phenyl        3-Methylphenyl                                                934                                                                               Phenyl        4-Methylphenyl                                                935                                                                               Phenyl        2,4-Dimethylphenyl                                            936                                                                               Phenyl        4-tert.-Butylphenyl                                           937                                                                               Phenyl        4-Methoxyphenyl                                               938                                                                               4-Fluorophenyl                                                                               4-Fluorophenyl                                                939                                                                               2-Fluorophenyl                                                                               4-Fluorophenyl                                                940                                                                               2-Chlorophenyl                                                                               4-Fluorophenyl                                                941                                                                               2-Chlorophenyl                                                                               2-Chlorophenyl                                                942                                                                               3-Chlorophenyl                                                                               3-Chlorophenyl                                                943                                                                               4-Chlorophenyl                                                                               4-Chlorophenyl                                                944                                                                               2-Chlorophenyl                                                                               4-Chlorophenyl                                                945                                                                               4-Methoxyphenyl                                                                              4-Methoxyphenyl                                               946                                                                               4-Dimethyl-   4-Dimethylaminophenyl                                            aminophenyl                                                                 947                                                                               Phenyl        Naphthyl                                                      948                                                                               Ethyl         Ethyl                                                         949                                                                               Ethyl         n-Propyl                                                      950                                                                               Ethyl         iso-Propyl                                                    951                                                                               Ethyl         n-Butyl                                                       952                                                                               Ethyl         iso-Butyl                                                     953                                                                               Ethyl         2-Methyl-butyl                                                954                                                                               Ethyl         Benzyl                                                        955                                                                               n-Propyl      n-Propyl                                                      956                                                                               iso-Propyl    iso-Propyl                                                    957                                                                               n-Butyl       n-Butyl                                                       958                                                                               iso-Butyl     iso-Butyl                                                     959                                                                               tert.-Butyl   tert.-Butyl                                                   960                                                                               Benzyl        Benzyl                                                        961                                                                               Pentachloroethyl                                                                             Pentachloroethyl                                              962                                                                               n-Hexyl       n-Hexyl                                                       963                                                                               Ethoxycarbonyl                                                                               Ethoxycarbonyl                                                964                                                                               Phenyl        Benzoyl                                                       965                                                                               Ethyl         Phenyl                                                        966                                                                               n-Butyl       Phenyl                                                        967                                                                               Styryl        Styryl                                                        968                                                                               2-Pyridyl     2-Pyridyl                                                     969                                                                               3-Pyridyl     3-Pyridyl                                                     970                                                                               Ethyl         2-Pyridyl         m.p.: 84-86° C.                      971                                                                                ##STR27##                      m.p.: 103-105° C.                    __________________________________________________________________________

                                      TABLE III                                    __________________________________________________________________________      ##STR28##                                                                     __________________________________________________________________________     No.                                                                               X      Y  R.sup.1                                                                            R.sup.2 = H                                                                         R.sup.3                                                                               R.sup.4     Data                                  __________________________________________________________________________     1  CHSCH.sub.3                                                                           O  CH.sub.3 CF.sub.3                                                                              Phenyl                                            2  CHSCH.sub.3                                                                           O  CH.sub.3 Cyclopropyl                                                                           Phenyl                                            3  CHSCH.sub.3                                                                           O  CH.sub.3 Cyclopropyl                                                                           4-Chlorophenyl                                    4  CHSCH.sub.3                                                                           O  CH.sub.3 Cyclopropyl                                                                           4-Methoxyphenyl                                   5  CHSCH.sub.3                                                                           O  CH.sub.3 Cyclopropyl                                                                           4-tert.-Butylphenyl                               6  CHSCH.sub.3                                                                           O  CH.sub.3 CN     Methylthio                                        7  CHSCH.sub.3                                                                           O  CH.sub.3 CN     2-Methoxyprop-2-yl                                8  CHSCH.sub.3                                                                           O  CH.sub.3 CN     2-Methylthioprop-2-yl                             9  CHSCH.sub.3                                                                           O  CH.sub.3 CN     Phenylthio                                        10 CHSCH.sub.3                                                                           O  CH.sub.3 CN     iso-Propyl                                        11 CHSCH.sub.3                                                                           O  CH.sub.3 CN     CN                                                12 CHSCH.sub.3                                                                           O  CH.sub.3 CN     Acetyl                                            13 CHSCH.sub.3                                                                           O  CH.sub.3 CN     Benzoyl                                           14 CHSCH.sub.3                                                                           O  CH.sub.3 CN     Methoxycarbonyl                                   15 CHSCH.sub.3                                                                           O  CH.sub.3 CN     Phenyl                                            __________________________________________________________________________     No.                                                                               X      Y  R.sup.1  R.sup.3                                                                               R.sup.4     Data                                  __________________________________________________________________________     16 CHSCH.sub.3                                                                           O  CH.sub.3 CN     2-Chlorophenyl                                    17 CHSCH.sub.3                                                                           O  CH.sub.3 CN     4-Chlorophenyl                                    18 CHSCH.sub.3                                                                           O  CH.sub.3 CN     2-Methylphenyl                                    19 CHSCH.sub.3                                                                           O  CH.sub.3 CN     4-tert.-Butylphenyl                               20 CHSCH.sub.3                                                                           O  CH.sub.3 CN     4-(n-Butoxyiminomethyl)                                                        phenyl                                            21 CHSCH.sub.3                                                                           O  CH.sub.3 CN     2-Pyridyl                                         22 CHSCH.sub.3                                                                           O  CH.sub.3 CN     Styryl                                            23 CHSCH.sub.3                                                                           O  CH.sub.3 CN     1-Propenyl                                        24 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              Phenylthio                                        25 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              Benzyl                                            26 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              tert.-Butyl                                       27 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              iso-Propyl                                        28 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              2-Methylbutyl                                     29 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              iso-Butyl                                         30 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              Phenyl                                            31 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              2-Chlorophenyl                                    32 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              4-Chlorophenyl                                    33 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              2-Methylphenyl                                    34 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              Naphthyl                                          35 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.3                                                                              1-Pryidyl                                         36 CHSCH.sub.3                                                                           O  CH.sub.3 iso-Butyl                                                                             iso-Butyl                                         37 CHSCH.sub.3                                                                           O  CH.sub.3 Phenyl Phenyl                                            38 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                      39 CHSCH.sub.3                                                                           O  CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2             40 CHCH.sub.3                                                                            O  CH.sub.3 CF.sub.3                                                                              Phenyl                                            41 CHCH.sub.3                                                                            O  CH.sub.3 Cyclopropyl                                                                           Phenyl                                            42 CHCH.sub.3                                                                            O  CH.sub.3 Cyclopropyl                                                                           4-Chlorophenyl                                    43 CHCH.sub.3                                                                            O  CH.sub.3 Cyclopropyl                                                                           4-Methoxyphenyl                                   44 CHCH.sub.3                                                                            O  CH.sub.3 Cyclopropyl                                                                           4-tert.-Butylphenyl                               45 CHCH.sub.3                                                                            O  CH.sub.3 CN     Methylthio                                        46 CHCH.sub.3                                                                            O  CH.sub.3 CN     2-Methoxyprop-2-yl                                                                         IR (film): 1717, 1436, 1367,                                                   1256, 1210, 1179,                                                              1070, 1037, 1009, 759                 47 CHCH.sub.3                                                                            O  CH.sub.3 CN     2-Methylthioprop-2-yl                                                                      .sup.1 H-NMR (CDCl.sub.3):                                                     δ  = 1.45s, 1.6d, 1.8s,                                                  3.7s,                                                                          5.1s, 7.1-7.5m                        48 CHCH.sub.3                                                                            O  CH.sub.3 CN     Phenylthio                                        49 CHCH.sub.3                                                                            O  CH.sub.3 CN     iso-Propyl  .sup.1 H-NMR (CDCl.sub.3):                                                     δ = 1.2d, 1.6d, 2.7m,                                                    3.67s,                                                                         5.1s, 7.0-7.5m                        50 CHCH.sub.3                                                                            O  CH.sub.3 CN     CN                                                51 CHCH.sub.3                                                                            O  CH.sub.3 CN     Acetyl                                            52 CHCH.sub.3                                                                            O  CH.sub.3 CN     Benzoyl                                           53 CHCH.sub.3                                                                            O  CH.sub.3 CN     Methoxycarbonyl                                   54 CHCH.sub.3                                                                            O  CH.sub.3 CN     Phenyl      .sup.1 H-NMR (CDCl.sub.3):                                                     δ = 1.6d, 3.7s, 5.2s,                                                    7.0-1.8m                              55 CHCH.sub.3                                                                            O  CH.sub.3 CN     2-Chlorophenyl                                    56 CHCH.sub.3                                                                            O  CH.sub.3 CN     4-Chlorophenyl                                    57 CHCH.sub.3                                                                            O  CH.sub.3 CN     2-Methylphenyl                                    58 CHCH.sub.3                                                                            O  CH.sub.3 CN     4-tert.-Butylphenyl                               59 CHCH.sub.3                                                                            O  CH.sub.3 CN     4-(n-Butoxyiminomethyl)                                                        phenyl                                            60 CHCH.sub.3                                                                            O  CH.sub.3 CN     2-Pyridyl                                         61 CHCH.sub.3                                                                            O  CH.sub.3 CN     Styryl                                            62 CHCH.sub.3                                                                            O  CH.sub.3 CN     1-Propenyl                                        63 CHCH.sub.3                                                                            O  CH.sub. 3                                                                               CH.sub.3                                                                              Phenylthio                                        64 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.3                                                                              Benzyl                                            65 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.3                                                                              tert.-Butyl                                       66 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.3                                                                              iso-Propyl                                        67 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.3                                                                              2-Methylbutyl                                     68 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.3                                                                              iso-Butyl                                         69 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.3                                                                              Phenyl                                            70 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.3                                                                              2-Chlorophenyl                                    71 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.3                                                                              4-Chlorophenyl                                                                             IR (film): 1716, 1490, 1434,                                                   1253, 1206, 1096,                                                              1036, 1012, 820, 760                  72 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.3                                                                              2-Methylphenyl                                    73 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.3                                                                              Naphthyl                                          74 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.3                                                                              1-Pryidyl                                         75 CHCH.sub.3                                                                            O  CH.sub.3 iso-Butyl                                                                             iso-Butyl                                         76 CHCH.sub.3                                                                            O  CH.sub.3 Phenyl Phenyl                                            77 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                      78 CHCH.sub.3                                                                            O  CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2             79 CH.sub.2                                                                              O  CH.sub.3  CF.sub.3                                                                             Phenyl                                            80 CH.sub.2                                                                              O  CH.sub.3 Cyclopropyl                                                                           Phenyl                                            81 CH.sub.2                                                                              O  CH.sub.3 Cyclopropyl                                                                           4-Chlorophenyl                                    82 CH.sub.2                                                                              O  CH.sub.3 Cyclopropyl                                                                           4-Methoxyphenyl                                   83 CH.sub.2                                                                              O  CH.sub.3 Cyclopropyl                                                                           4-tert.-Butylphenyl                               84 CH.sub.2                                                                              O  CH.sub.3 CN     Methylthio                                        85 CH.sub.2                                                                              O  CH.sub.3 CN     2-Methoxyprop-2-yl                                86 CH.sub.2                                                                              O  CH.sub.3 CN     2-Methylthioprop-2-yl                             87 CH.sub.2                                                                              O  CH.sub.3 CN     Phenylthio                                        88 CH.sub.2                                                                              O  CH.sub.3 CN     iso-Propyl                                        89 CH.sub.2                                                                              O  CH.sub.3 CN     CN                                                90 CH.sub.2                                                                              O  CH.sub.3 CN     Acetyl                                            91 CH.sub.2                                                                              O  CH.sub.3 CN     Benzoyl                                           92 CH.sub.2                                                                              O  CH.sub.3 CN     Methoxycarbonyl                                   93 CH.sub.2                                                                              O  CH.sub.3 CN     Phenyl                                            94 CH.sub.2                                                                              O  CH.sub.3 CN     2-Chlorophenyl                                    95 CH.sub.2                                                                              O  CH.sub.3 CN     4-Chlorophenyl                                    96 CH.sub.2                                                                              O  CH.sub.3 CN     2-Methylphenyl                                    97 CH.sub.2                                                                              O  CH.sub.3 CN     4-tert.-Butylphenyl                               98 CH.sub.2                                                                              O  CH.sub.3 CN     4-(n-Butoxyiminomethyl)                                                        phenyl                                            99 CH.sub.2                                                                              O  CH.sub.3 CN     2-Pyridyl                                         100                                                                               CH.sub.2                                                                              O  CH.sub.3 CN     Styryl                                            101                                                                               CH.sub.2                                                                              O  CH.sub.3 CN     1-Propenyl                                        102                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              Phenylthio                                        103                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              Benzyl                                            104                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              tert.-Butyl                                       105                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              iso-Propyl                                        106                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              2-Methylbutyl                                     107                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              iso-Butyl                                         108                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              Phenyl                                            109                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              2-Chlorophenyl                                    110                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              4-Chlorophenyl                                    111                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              2-Methylphenyl                                    112                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              Naphthyl                                          113                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.3                                                                              1-Pryidyl                                         114                                                                               CH.sub.2                                                                              O  CH.sub.3 iso-Butyl                                                                             iso-Butyl                                         115                                                                               CH.sub.2                                                                              O  CH.sub.3 Phenyl Phenyl                                            116                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                      117                                                                               CH.sub.2                                                                              O  CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2             118                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CF.sub.3                                                                              Phenyl                                            119                                                                               NOCH.sub.3                                                                            S  CH.sub.3 Cyclopropyl                                                                           Phenyl                                            120                                                                               NOCH.sub.3                                                                            S  CH.sub.3 Cyclopropyl                                                                           4-Chlorophenyl                                    121                                                                               NOCH.sub.3                                                                            S  CH.sub.3 Cyclopropyl                                                                           4-Methoxyphenyl                                   122                                                                               NOCH.sub.3                                                                            S  CH.sub.3 Cyclopropyl                                                                           4-tert.-Butylphenyl                               123                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     Methylthio                                        124                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     2-Methoxyprop-2-yl                                125                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     2-Methylthioprop-2-yl                             126                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     Phenylthio                                        127                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     iso-Propyl                                        128                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     CN                                                129                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     Acetyl                                            130                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     Benzoyl                                           131                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     Methoxycarbonyl                                   132                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     Phenyl                                            133                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     2-Chlorophenyl                                    134                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     4-Chlorophenyl                                    135                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     2-Methylphenyl                                    136                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     4-tert.-Butylphenyl                               137                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     4-(n-Butoxyiminomethyl)                                                        phenyl                                            138                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     2-Pyridyl                                         139                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     Styryl                                            140                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CN     1-Propenyl                                        141                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.3                                                                              Phenylthio                                        142                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.3                                                                              Benzyl                                            143                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.3                                                                              tert.-Butyl                                       144                                                                               NOCH.sub.3                                                                            S  CH.sub. 3                                                                               CH.sub.3                                                                              iso-Propyl                                        145                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.3                                                                              2-Methylbutyl                                     146                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.3                                                                              iso-Butyl                                         147                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.3                                                                              Phenyl                                            148                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.3                                                                              2-Chlorophenyl                                    149                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.3                                                                              4-Chlorophenyl                                    150                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.3                                                                              2-Methylphenyl                                    151                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.3                                                                              Naphthyl                                          152                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.3                                                                              1-Pryidyl                                         153                                                                               NOCH.sub.3                                                                            S  CH.sub.3 iso-Butyl                                                                             iso-Butyl                                         154                                                                               NOCH.sub.3                                                                            S  CH.sub.3 Phenyl Phenyl                                            155                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                      156                                                                               NOCH.sub.3                                                                            S  CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2             157                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CF.sub.3                                                                              Phenyl                                            158                                                                               NOCH.sub.3                                                                            NH CH.sub.3 Cyclopropyl                                                                           Phenyl                                            159                                                                               NOCH.sub.3                                                                            NH CH.sub.3 Cyclopropyl                                                                           4-Chlorophenyl                                                                             m.p.: 71-74° C.                                                         IR (KBr): 3348, 1663, 1529,                                                    1042, 1030, 982                       160                                                                               NOCH.sub.3                                                                            NH CH.sub.3 Cyclopropyl                                                                           4-Methoxyphenyl                                   161                                                                               NOCH.sub.3                                                                            NH CH.sub.3 Cyclopropyl                                                                           4-tert.-Butylphenyl                               162                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     Methylthio                                        163                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     2-Methoxyprop-2-yl                                164                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     2-Methylthioprop-2-yl                             165                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     Phenylthio                                        166                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     iso-Propyl                                        167                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     CN                                                168                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     Acetyl                                            169                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     Benzoyl                                           170                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     Methoxycarbonyl                                   171                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     Phenyl                                            172                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     2-Chlorophenyl                                    173                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     4-Chlorophenyl                                    174                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     2-Methylphenyl                                    175                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     4-tert.-Butylphenyl                               176                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     4-(n-Butoxyiminomethyl)                                                        phenyl                                            177                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     2-Pyridyl                                         178                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     Styryl                                            179                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CN     1-Propenyl                                        180                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              Phenylthio                                        181                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub. 3                                                                             Benzyl                                            182                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              tert.-Butyl                                       183                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              iso-Propyl                                        184                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              2-Methylbutyl                                     185                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              iso-Butyl                                         186                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              Phenyl                                            187                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              2-Chlorophenyl                                    188                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              4-Chlorophenyl                                                                             m.p.: 119-121° C.                                                       IR (KBr): 3421, 1676, 1037, 985,                                               933, 752                              189                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              2-Methylphenyl                                    __________________________________________________________________________     No.                                                                               X      Y  R.sup.1                                                                            R.sup.2                                                                             R.sup.3                                                                               R.sup.4     Data                                  __________________________________________________________________________     190                                                                               NOCH.sub.3                                                                            NH CH.sub.3                                                                           H    CH.sub.3                                                                              Naphthyl                                          191                                                                               NOCH.sub.3                                                                            NH CH.sub.3                                                                           H    CH.sub.3                                                                              1-Pryidyl                                         192                                                                               NOCH.sub.3                                                                            NH CH.sub.3                                                                           H    iso-Butyl                                                                             iso-Butyl                                         193                                                                               NOCH.sub.3                                                                            NH CH.sub.3                                                                           H    Phenyl Phenyl                                            194                                                                               NOCH.sub.3                                                                            NH CH.sub.3                                                                           H    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                      195                                                                               NOCH.sub.3                                                                            NH CH.sub.3                                                                           H    CH.sub.2 CH.sub. 2 CH.sub.2 CH.sub.2 CH.sub.2            196                                                                               NOCH.sub.3                                                                            O  C.sub.2 H.sub.5                                                                    H    CH.sub.3                                                                              Phenyl                                            197                                                                               CHOCH.sub.3                                                                           O  C.sub.2 H.sub.5                                                                    H    CH.sub.3                                                                              Phenyl                                            198                                                                               NOCH.sub.3                                                                            O  n-C.sub.3 H.sub.5                                                                  H    CH.sub.3                                                                              Phenyl                                            199                                                                               CHOCH.sub.3                                                                           O  n-C.sub.3 H.sub.5                                                                  H    CH.sub.3                                                                              Phenyl                                            200                                                                               CHC.sub.2 H.sub.5                                                                     O  CH.sub.3                                                                           H    CH.sub.3                                                                              Phenyl                                            201                                                                               NOCH.sub.3                                                                            O  CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                              Phenyl                                            202                                                                               CHOCH.sub.3                                                                           O  CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                              Phenyl                                            203                                                                               NOCH.sub.3                                                                            O  CH.sub.3                                                                           CH.sub.3                                                                            CN     Phenyl                                            204                                                                               CHOCH.sub.3                                                                           O  CH.sub.3                                                                           CH.sub.3                                                                            CN     Phenyl                                            205                                                                               CHSCH.sub.3                                                                           O  CH.sub.3                                                                           H    H      Phenyl                                            206                                                                               CHCH.sub.3                                                                            O  CH.sub.3                                                                           H    H      Phenyl                                            207                                                                               CH.sub.2                                                                              O  CH.sub.3                                                                           H    H      Phenyl                                            208                                                                               NOCH.sub.3                                                                            S  CH.sub.3                                                                           H    H      Phenyl                                            209                                                                               CHOCH.sub.3                                                                           S  CH.sub.3                                                                           H    H      Phenyl                                            210                                                                               CHOCH.sub.3                                                                           NH CH.sub.3                                                                           H    H      Phenyl                                            211                                                                               NOCH.sub.3                                                                            NH CH.sub.3                                                                           H    H      Phenyl                                            212                                                                               CHOCH.sub.3                                                                           S  CH.sub.3                                                                           H    CN     Methylthio                                        __________________________________________________________________________     No.                                                                               X      Y  R.sup.1                                                                            R.sup.2 = H                                                                         R.sup.3                                                                               R.sup.4     Data                                  __________________________________________________________________________     213                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     2-Methoxyprop-2-yl                                214                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     2-Methylthioprop-2-yl                             215                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     Phenylthio                                        216                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     iso-Propyl                                        217                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     CN                                                218                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     Acetyl                                            219                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     Benzoyl                                           220                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     Methoxycarbonyl                                   221                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     Phenyl                                            222                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     2-Chlorophenyl                                    223                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     4-Chlorophenyl                                    224                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     2-Methylphenyl                                    225                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     4-tert.-Butylphenyl                               226                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     4-(n-Butoxyiminomethyl)                                                        phenyl                                            227                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     2-Pyridyl                                         228                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     Styryl                                            229                                                                               CHOCH.sub.3                                                                           S  CH.sub.3 CN     1-Propenyl                                        230                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     Methylthio                                        231                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     2-Methoxyprop-2-yl                                232                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     2-Methylthioprop-2-yl                             233                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     Phenylthio                                        234                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     iso-Propyl                                        235                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     CN                                                236                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     Acetyl                                            237                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     Benzoyl                                           238                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     Methoxycarbonyl                                   239                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     Phenyl                                            240                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     2-Chlorophenyl                                    241                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     4-Chlorophenyl                                    242                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     2-Methylphenyl                                    243                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     4-tert.-Butylphenyl                               244                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     4-(n-Butoxyiminomethyl)                                                        phenyl                                            245                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     2-Pyridyl                                         246                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     Styryl                                            247                                                                               CHOCH.sub.3                                                                           NH CH.sub.3 CN     1-Propenyl                                        248                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              3-Chlorphenyl                                                                              m.p.: 71-74° C.;               249                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              3,5-Dichlorphenyl                                                                          m.p.: 94-97° C.;               250                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              2,3,4-Trichlorphenyl                                                                       m.p.: 110-112° C.;             251                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              3-Bromphenyl                                                                               m.p.: 74-77° C.;               252                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              4-Methylphenyl                                                                             m.p.: 69-72° C.;               253                                                                               NOCH.sub.3                                                                            NH CH.sub.3 CH.sub.3                                                                              4-Nitrophenyl                                                                              m.p.: 134-137° C.;             254                                                                               CHCH.sub.3                                                                            O  CH.sub.3 CN     2-Ethoxy-prop-2-yl                                                                         IR (film): 2982, 1717, 1436,                                                   1255, 1210, 1192,                                                              1067, 1037, 1010                      255                                                                               CHCH.sub.3                                                                            O  CH.sub.3 CN     2-i-Propoxy-prop-2-yl                                                                      IR (film): 2983, 1718, 1383,                                                   1370, 1255, 1173,                                                              1119, 1109, 1037, 1002                256                                                                               CHCH.sub.3                                                                            O  CH.sub.3 CN     2-n-Butoxy-prop-2-yl                                                                       IR (film): 2957, 1718, 1435,                                                   1255, 1176, 1036,                                                              1010, 759                             257                                                                               CHCH.sub.3                                                                            O  CH.sub.3 CN     2-i-Butoxy-prop-2-yl                                                                       IR (film): 2956, 1717, 1435,                                                   1366, 1255, 1209,                                                              1176, 1064, 1037, 1008                258                                                                               CHCH.sub.3                                                                            O  CH.sub.3 CN     Cyclopropyl .sup. 1 H-NMR (CDCl.sub.3):                                                    δ = 0.9m, 1.6d, 2.3m,                                                    3.67s, 5.15s, 7.05-7.4m               259                                                                               CHCH.sub.3                                                                            O  CH.sub.3 CN     2-Ethylthio-prop-2-yl                                                                      .sup.1 H-NMR (CDCl.sub.3):                                                     δ = 1.1t, 1.5s, 1.6d,                                                    2.2q,                                                                          3.7s, 5.1s, 7.1-7.5m                  260                                                                               CHCH.sub.3                                                                            O  CH.sub.3 CN     2-i-Propylthio-pro-2-yl                                                                    .sup.1 H-NMR (CDCl.sub.3):                                                     δ = 1.15s, 1.5s, 1.6d,                                                   2.6m,                                                                          3.7s, 5.1s, 7.1-7.5m                  261                                                                               CHCH.sub.3                                                                            O  CH.sub.3 CN     2-Tetrahydropyranyl                                                                        .sup.1 H-NMR (CDCl.sub.3):                                                     δ = 1.4-1.9m, 1.6d, 3.5m,                                                3.7s, 4.1m, 5.1s,                     __________________________________________________________________________                                              7.0-7.5m                         

                                      TABLE IV                                     __________________________________________________________________________      ##STR29##                                                                     No.                                                                               X     Y R.sup.1                                                                           R.sup.3                                                                           R.sup.4    Data                                               __________________________________________________________________________     1  CHOCH.sub.3                                                                          O CH.sub.3                                                                          CH.sub.3                                                                          Phenyl                                                        2  CHOCH.sub.3                                                                          O CH.sub.3                                                                          CH.sub.3                                                                          3-Bromophenyl                                                 3  CHOCH.sub.3                                                                          O CH.sub.3                                                                          CH.sub.3                                                                          4-Phenoxyphenyl                                               4  CHOCH.sub.3                                                                          O CH.sub.3                                                                          CH.sub.3                                                                          4-Cyclohexylphenyl                                            5  NOCH.sub.3                                                                           O CH.sub.3                                                                          CH.sub.3                                                                          Phenyl                                                        6  NOCH.sub.3                                                                           O CH.sub.3                                                                          CH.sub.3                                                                          3-Bromophenyl                                                                             oil; IR (film): 1727, 1436, 1312, 1240, 1032       7  NOCH.sub.3                                                                           O CH.sub.3                                                                          CH.sub.3                                                                          4-Phenoxyphenyl                                                                           oil; IR (film): 1727, 1489, 1239, 1031, 683        8  NOCH.sub.3                                                                           O CH.sub.3                                                                          CH.sub.3                                                                          4-Cyclohexylphenyl                                                                        oil; IR (film): 2925, 1728, 1447, 1239, 1164,                                  1077, 1032                                         9  CHOCH.sub.3                                                                          O CH.sub.3                                                                          CN iso-Propyl oil; IR (film): 2970, 2220, 1710, 1127             10 CHOCH.sub.3                                                                          O CH.sub.3                                                                          CN 2-Methoxyprop-2-yl                                                                        oil; IR (film): 2980, 2220, 1710, 1127             11 CHOCH.sub.3                                                                          O CH.sub.3                                                                          CN 2-Methylthioprop-2-yl                                                                     oil; IR (film): 2980, 2220, 1709, 1127             12 CHOCH.sub.3                                                                          O CH.sub.3                                                                          CN 2-Tetrahydrofuranyl                                                                       oil; IR (film): 2945, 2850, 2220, 1709, 1127       13 CHOCH.sub.3                                                                          O CH.sub.3                                                                          CN Phenyl     oil; IR (film): 2940, 2220, 1709, 1127,            __________________________________________________________________________                                 1030                                          

                                      TABLE V                                      __________________________________________________________________________      ##STR30##                                                                     No.                                                                               R.sup.3                                                                           R.sup.4           Data                                                   __________________________________________________________________________      1 H  H                                                                         2 H  Methoxymethyl                                                             3 H  Ethoxymethyl                                                              4 H  n-Propoxymethyl                                                           5 H  iso-Propoxymethyl                                                         6 H  tert.-Butoxymethyl                                                        7 H  2-Methoxyprop-2-yl                                                        8 H  2-Ethoxyprop-2-yl                                                         9 H  2-n-Propoxyprop-2-yl                                                      10                                                                               H  2-iso-Propoxyprop-2-yl                                                    11                                                                               H  2-tert.-Butoxyprop-2-yl                                                   12                                                                               H  Methylthiomethyl                                                          13                                                                               H  tert.-Butylthiomethyl                                                     14                                                                               H  2-Methylthioprop-2-yl                                                     15                                                                               H  2-iso-Propylthioprop-2-yl                                                 16                                                                               H  2-tert.-Butylthioprop-2-yl                                                17                                                                               H  Methyl                                                                    18                                                                               H  Ethyl                                                                     19                                                                               H  n-Propyl                                                                  20                                                                               H  iso-Propyl                                                                21                                                                               H  n-Butyl                                                                   22                                                                               H  iso-Butyl                                                                 23                                                                               H  sec.-Butyl                                                                24                                                                               H  tert.-Butyl                                                               25                                                                               H  n-Hexyl                                                                   26                                                                               H  n-Decyl                                                                   27                                                                               H  Cyclopropyl                                                               28                                                                               H  Cyclohexyl                                                                29                                                                               H  Phenylthiomethyl                                                          30                                                                               H  2-Phenylthiomethyl                                                        31                                                                               H  2-(2'-Chlorophenylthio)prop-2-yl                                          32                                                                               H  Ethynyl                                                                   33                                                                               H  1-Propynyl                                                                34                                                                               H  Methoxy                                                                   35                                                                               H  Ethoxy                                                                    36                                                                               H  n-Propoxy                                                                 37                                                                               H  iso-Propoxy                                                               38                                                                               H  n-Butoxy                                                                  39                                                                               H  iso-Butoxy                                                                40                                                                               H  sec.-Butoxy                                                               41                                                                               H  tert.-Butoxy                                                              42                                                                               H  Methylthio                                                                43                                                                               H  Ethylthio                                                                 44                                                                               H  n-Propylthio                                                              45                                                                               H  iso-Propylthio                                                            46                                                                               H  n-Butylthio                                                               47                                                                               H  iso-Butylthio                                                             48                                                                               H  sec.-Butylthio                                                            49                                                                               H  tert.-Butylthio                                                           50                                                                               H  Benzylthio                                                                51                                                                               H  Trifluoromethoxy                                                          52                                                                               H  Cyano                                                                     53                                                                               H  Amino                                                                     54                                                                               H  Methylamino                                                               55                                                                               H  Dimethylamino                                                             56                                                                               H  Ethylamino                                                                57                                                                               H  Diethylamino                                                              58                                                                               H  Di-n-Propylamino                                                          59                                                                               H  Di-iso-Propylamino                                                        60                                                                               H  Di-n-Butylamino                                                           61                                                                               H  Di-iso-Butylamino                                                         62                                                                               H  Acetyl                                                                    63                                                                               H  Propion-1-yl                                                              64                                                                               H  Butyr-1-yl                                                                65                                                                               H  iso-Butyr-1-yl                                                            66                                                                               H  Pivaloyl                                                                  67                                                                               H  Benzoyl                                                                   68                                                                               H  4-Chlorobenzoyl                                                           69                                                                               H  Benzylcarbonyl                                                            70                                                                               H  Methoxycarbonyl                                                           71                                                                               H  Ethoxycarbonyl                                                            72                                                                               H  n-Propoxycarbonyl                                                         73                                                                               H  iso-Propoxycarbonyl                                                       74                                                                               H  n-Butoxycarbonyl                                                          75                                                                               H  iso-Butoxycarbonyl                                                        76                                                                               H  sec.-Butoxycarbonyl                                                       77                                                                               H  tert.-Butoxycarbonyl                                                      78                                                                               H  n-Hexoxycarbonyl                                                          79                                                                               H  Phenoxycarbonyl                                                           80                                                                               H  4-Chlorphenoxycarbonyl                                                    81                                                                               H  Benzyloxycarbonyl                                                         82                                                                               H  Aminocarbonyl                                                             83                                                                               H  Dimethylaminocarbonyl                                                     84                                                                               H  Diethylaminocarbonyl                                                      85                                                                               H  Di-iso-Propylaminocarbonyl                                                86                                                                               H  Phenylaminocarbonyl                                                       87                                                                               H  N-Methyl-N-Phenylaminocarbonyl                                            88                                                                               H  Phenyl                                                                    89                                                                               H  2-Fluorophenyl    m.p.: 69-71° C.;                                 90                                                                               H  3-Fluorophenyl    m.p.: 74-77° C.;                                 91                                                                               H  4-Fluorophenyl    m.p.: 73-76° C.; IR (KBr): 1699,                                        1278, 1271, 1256, 1225                                  92                                                                               H  Pentafluorophenyl m.p.: 94-96° C.; IR (KBr): 1704,                                        1527, 1494, 1133                                        93                                                                               H  2-Chlorophenyl    .sup.1 H-NMR(CDCl.sub.3): δ = 3.70s,                                     3.82s, 5.15s, 7.15-7.40m,                                                      7.52m, 7.60s, 7.85m, 8.52s                              94                                                                               H  3-Chlorophenyl    m.p.: 48-50° C.;                                 95                                                                               H  4-Chlorophenyl    (v. Exaample 6)                                         96                                                                               H  Pentachlorophenyl                                                         97                                                                               H  2,3-Dichlorophenyl                                                                               m.p.: 103-105° C.;                               98                                                                               H  2,4-Dichlorophenyl                                                                               m.p.: 94-96° C.;                                 99                                                                               H  2,5-Dichlorophenyl                                                       100                                                                               H  2,6-Dichlorophenyl                                                                               m.p.: 118-120° C.;                              101                                                                               H  3,4-Dichlorophenyl                                                                               m.p.: 82-84° C.;                                102                                                                               H  3,5-Dichlorophenyl                                                                               m.p.: 94-96° C.;                                103                                                                               H  2,3,4-Trichlorophenyl                                                    104                                                                               H  2,3,5-Trichlorophenyl                                                    105                                                                               H  2,3,6-Trichlorophenyl                                                    106                                                                               H  2,4,5-Trichlorophenyl                                                    107                                                                               H  2,4,6-Trichlorophenyl                                                    108                                                                               H  3,4,5-Trichlorophenyl                                                    109                                                                               H  2,3,4,6-Tetrachlorophenyl                                                110                                                                               H  2,3,5,6-Tetrachlorophenyl                                                111                                                                               H  2-Bromophenyl     m.p.: 85-87° C.;                                112                                                                               H  3-Bromophenyl     .sup.1 H-NMR (CDCl.sub.3): δ = 3.68s,                                    3.79s, 5.13, 7.15-7.54m, 7.59s                                                 7.74s, 8.00s                                           113                                                                               H  4-Bromophenyl     m.p.: 131-134° C.;                              114                                                                               H  2,4-Dibromophenyl                                                        115                                                                               H  3-Brom-4-fluorophenyl                                                    116                                                                               H  3-Brom-4-methoxyphenyl                                                   117                                                                               H  2-Iodophenyl                                                             118                                                                               H  3-Iodophenyl                                                             119                                                                               H  4-Iodophenyl                                                             120                                                                               H  2-Chloro-4-fluorophenyl                                                                          m.p.: 112-115° C.;                              121                                                                               H  2-Chloro-5-fluorophenyl                                                  122                                                                               H  2-Chloro-6-fluorophenyl                                                                          m.p.: 80-82° C.;                                123                                                                               H  2-Chloro-4-bromophenyl                                                   124                                                                               H  2-Bromo-4-chlorophenyl                                                   125                                                                               H  2-Bromo-4-fluorophenyl                                                   126                                                                               H  3-Bromo-4-chlorophenyl                                                   127                                                                               H  3-Chloro-4-fluorophenyl                                                  128                                                                               H  3-Fluoro-4-chlorophenyl                                                  129                                                                               H  2-Cyanophenyl                                                            130                                                                               H  3-Cyanophenyl                                                            131                                                                               H  4-Cyanophenyl                                                            132                                                                               H  2-Nitrophenyl                                                            133                                                                               H  3-Nitrophenyl                                                            134                                                                               H  4-Nitrophenyl     m.p.: 147-155° C.;                              135                                                                               H  2-Methylphenyl    m.p.: 57-59° C.;                                136                                                                               H  3-Methylphenyl    m.p.: 54-56° C.;                                137                                                                               H  4-Methylphenyl    m.p.: 86-88° C.;                                138                                                                               H  2,4-Dimethylphenyl                                                                               m.p.: 75-77° C.;                                139                                                                               H  2,6-Dimethylphenyl                                                       140                                                                               H  3,4-Dimethylphenyl                                                       141                                                                               H  3,5-Dimethylphenyl                                                       142                                                                               H  2,3,4-Trimethylphenyl                                                    143                                                                               H  2,3,5-Trimethylphenyl                                                    144                                                                               H  2,3,6-Trimethylphenyl                                                    145                                                                               H  2,4,5-Trimethylphenyl                                                    146                                                                               H  2,4,6-Trimethylphenyl                                                    147                                                                               H  3,4,5-Trimethylphenyl                                                    148                                                                               H  Pentamethylphenyl                                                        149                                                                               H  2-Ethylphenyl                                                            150                                                                               H  3-Ethylphenyl                                                            151                                                                               H  4-Ethylphenyl                                                            152                                                                               H  3,5-Diethylphenyl                                                        153                                                                               H  2-n-Propylphenyl                                                         154                                                                               H  3-n-Propylphenyl                                                         155                                                                               H  4-n-Propylphenyl                                                         156                                                                               H  2-iso-Propylphenyl                                                       157                                                                               H  3-iso-propylphenyl                                                       158                                                                               H  4-iso-Propylphenyl                                                       159                                                                               H  2,4-Di-iso-Propylphenyl                                                  160                                                                               H  3,5-Di-iso-Propylphenyl                                                  161                                                                               H  4-n-Butylphenyl                                                          162                                                                               H  4-sec.-Butylphenyl                                                       163                                                                               H  4-iso-Butylphenyl                                                        164                                                                               H  4-tert.-Butylphenyl                                                                              m.p.: 71-73° C.                                 165                                                                               H  3-tert.-Butylphenyl                                                      166                                                                               H  2-tert.-Butylphenyl                                                      167                                                                               H  2,4-Di-tert.-Butylphenyl                                                 168                                                                               H  3,5-Di-tert.-Butylphenyl                                                 169                                                                               H  4-n-Hexylphenyl                                                          170                                                                               H  4-n-Dodecylphenyl                                                        171                                                                               H  2-Methyl-4-tert.-Butylphenyl                                             172                                                                               H  2-methyl-6-tert.-Butylphenyl                                             173                                                                               H  2-Methyl-4-iso-Propylphenyl                                              174                                                                               H  2-Methyl-4-cyclohexylphenyl                                              175                                                                               H  2-Methyl-4-phenylphenyl                                                  176                                                                               H  2-Methyl-4-benzylphenyl                                                  177                                                                               H  2-Methyl-4-phenoxyphenyl                                                 178                                                                               H  2-Methyl-4-benzyloxyphenyl                                               179                                                                               H  2-Methyl-3-chlorophenyl                                                  180                                                                               H  2-Methyl-4-chlorophenyl                                                  181                                                                               H  2-Methyl-5-chlorophenyl                                                  182                                                                               H  2-Methyl-6-chlorophenyl                                                  183                                                                               H  2-Methyl-4-fluorophenyl                                                  184                                                                               H  2-Methyl-3-bromophenyl                                                   185                                                                               H  2-Methyl-4-bromophenyl                                                   186                                                                               H  2-Methyl-3-methoxyphenyl                                                 187                                                                               H  2-Methyl-4-methoxyphenyl                                                 188                                                                               H  2-Methyl-5-methoxyphenyl                                                 189                                                                               H  2-Methyl-6-methoxyphenyl                                                 190                                                                               H  2-Methyl-4-iso-Propoxyphenyl                                             191                                                                               H  2-Methyl-2,5-dimethoxyphenyl                                             192                                                                               H  2-Methoxyphenyl   m.p.: 52-54° C.                                 193                                                                               H  3-Methoxyphenyl   .sup.1 H-NMR (CDCl.sub.3): δ = 3.65s,                                    3.76s, 3.80s, 5.12s,                                                           6.88-7.54m, 7.58s, 8.05s                               194                                                                               H  4-Methoxyphenyl   m.p.: 61-63° C.                                 195                                                                               H  2,3-Dimethoxyphenyl                                                      196                                                                               H  2,4-Dimethoxyphenyl                                                                              m.p.: 70-72° C.                                 197                                                                               H  2,5-Dimethoxyphenyl                                                      198                                                                               H  2,6-Dimethoxyphenyl                                                      199                                                                               H  3,4-Dimethoxyphenyl                                                      200                                                                               H  3,5-Dimethoxyphenyl                                                                              m.p.: 79-82° C.                                 201                                                                               H  3,6-Dimethoxyphenyl                                                      202                                                                               H  2,3,4-Trimethoxyphenyl                                                   203                                                                               H  2,3,5-Trimethoxyphenyl                                                   204                                                                               H  2,3,6-Trimethoxyphenyl                                                   205                                                                               H  2,4,5-Trimethoxyphenyl                                                   206                                                                               H  2,4,6-Trimethoxyphenyl                                                   207                                                                               H  3,4,5-Trimethoxyphenyl                                                   208                                                                               H  2-Ethoxyphenyl                                                           209                                                                               H  3-Ethoxyphenyl    .sup.1 H-NMR (CDCl.sub.3): δ = 1.39t,                                    3.67s, 3.80s, 4.02q, 5.12s,                                                    6.87-7.54m, 7.58s, 8.05s                               210                                                                               H  4-Ethoxyphenyl    m.p.: 93-94° C.                                 211                                                                               H  2-iso-Propoxyphenyl                                                      212                                                                               H  3-iso-Propoxyphenyl                                                      213                                                                               H  4-iso-Propoxyphenyl                                                      214                                                                               H  3-tert.-Butoxyphenyl                                                     215                                                                               H  4-tert.-Butoxyphenyl                                                                             .sup.1 H-NMR (CDCl.sub.3): δ = 1.36s,                                    3.68s, 3.78s, 5.09s,                                                           6.94-7.53m, 7.58s, 8.07s                               216                                                                               H  2-Trifluoromethoxyphenyl                                                 217                                                                               H  3-Trifluoromethoxyphenyl                                                 218                                                                               H  4-Trifluoromethoxyphenyl                                                 219                                                                               H  3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                                  220                                                                               H  4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                                  221                                                                               H  2-Chloromethylphenyl                                                     222                                                                               H  3-Chloromethylphenyl                                                     223                                                                               H  4-Chloromethylphenyl                                                     224                                                                               H  2-Trifluoromethylphenyl                                                                          m.p.: 75-77° C.                                 225                                                                               H  3-Trifluoromethylphenyl                                                  226                                                                               H  4-Trifluoromethylphenyl                                                                          m.p.: 111-114° C.                               227                                                                               H  2-(Methoxyiminomethyl)phenyl                                             228                                                                               H  3-(Methoxyiminomethyl)phenyl                                             229                                                                               H  4-(Methoxyiminomethyl)phenyl                                             230                                                                               H  2-(Ethoxyiminomethyl)phenyl                                              231                                                                               H  3-(Ethoxyiminomethyl)phenyl                                              232                                                                               H  4-(Ethoxyiminomethyl)phenyl                                              233                                                                               H  2-(n-Propoxyiminomethyl)phenyl                                           234                                                                               H  3-(n-Propoxyiminomethyl)phenyl                                           235                                                                               H  4-(n-Propoxyiminomethyl)phenyl                                           236                                                                               H  2-(iso-Propoxyiminomethyl)phenyl                                         237                                                                               H  3-(iso-Propoxyiminomethyl)phenyl                                         238                                                                               H  4-(iso-Propoxyiminomethyl)phenyl                                         239                                                                               H  2-(n-Butoxyiminomethyl)phenyl                                            240                                                                               H  3-(n-Butoxyiminomethyl)phenyl                                            241                                                                               H  4-(n-Butoxyiminomethyl)phenyl                                            242                                                                               H  2-(iso-outoxyiminomethyl)phenyl                                          243                                                                               H  3-(iso-Butoxyiminomethyl)phenyl                                          244                                                                               H  4-(iso-Butoxyiminomethyl)phenyl                                          245                                                                               H  2-(tert.-Butoxyiminomethyl)phenyl                                        246                                                                               H  3-(tert.-Butoxyiminomethyl)phenyl                                        247                                                                               H  4-(tert.-Butoxyiminomethyl)phenyl                                        248                                                                               H  2-(n-Pentoxyiminomethyl)phenyl                                           249                                                                               H  3-(n-Pentoxyiminomethyl)phenyl                                           250                                                                               H  4-(n-Pentoxyiminomethyl)phenyl                                           251                                                                               H  2-(n-Hexoxyiminomethyl)phenyl                                            252                                                                               H  3-(n-Hexoxyiminomethyl)phenyl                                            253                                                                               H  4-(n-Hexoxyiminomethyl)phenyl                                            254                                                                               H  2-(Allyloxyiminomethyl)phenyl                                            255                                                                               H  3-(Allyloxyiminomethyl)phenyl                                            256                                                                               H  4-(Allyloxyiminomethyl)phenyl                                            257                                                                               H  2-(Benzyloxyiminomethyl)phenyl                                           258                                                                               H  3-(Benzyloxyiminomethyl)phenyl                                           259                                                                               H  4-(Benzyloxyiminomethyl)phenyl                                           260                                                                               H  2-(Methoxyimino-1'-ethyl)phenyl                                          261                                                                               H  3-(Methoxyimino-1'-ethyl)phenyl                                          262                                                                               H  4-(Methoxyimino-1'-ethyl)phenyl                                          263                                                                               H  2-(Ethoxyimino-1'-ethyl)phenyl                                           264                                                                               H  3-(Ethoxyimino-1'-ethyl)phenyl                                           265                                                                               H  4-(Ethoxyimino-1'-ethyl)phenyl                                           266                                                                               H  2-(n-Propoxyimino-1'-ethyl)phenyl                                        267                                                                               H  3-(n-Propoxyimino-1'-ethyl)phenyl                                        268                                                                               H  4-(n-Propoxyimino-1'-ethyl)phenyl                                        269                                                                               H  2-(n-Butoxyamino-1'-ethyl)phenyl                                         270                                                                               H  3-(n-Butoxyamino-1'-ethyl)phenyl                                         271                                                                               H  4-(n-Butoxyamino-1'-ethyl)phenyl                                         272                                                                               H  2-(n-Pentoxyimino-1'-ethyl)phenyl                                        273                                                                               H  3-(n-Pentoxyimino-1'-ethyl)phenyl                                        274                                                                               H  4-(n-Pentoxyimino-1'-ethyl)phenyl                                        275                                                                               H  2-(n-Hexoxyimino-1'-ethyl)phenyl                                         276                                                                               H  3-(n-Hexoxyimino-1'-ethyl)phenyl                                         277                                                                               H  4-(n-Hexoxyimino-1'-ethyl)phenyl                                         278                                                                               H  2-(Allyloxyimino-1'-ethyl)phenyl                                         279                                                                               H  3-(Allyloxyimino-1'-ethyl)phenyl                                         280                                                                               H  4-(Allyloxyimino-1'-ethyl)phenyl                                         281                                                                               H  2-(Benzyloxyimino-1'-ethyl)phenyl                                        282                                                                               H  3-(Benzyloxyimino-1'-ethyl)phenyl                                        283                                                                               H  4-(Benzyloxyimino-1'-ethyl)phenyl                                        284                                                                               H  2-Phenylphenyl                                                           285                                                                               H  3-Phenylphenyl                                                           286                                                                               H  4-Phenylphenyl    m.p.: 94-96° C.                                 287                                                                               H  2-Phenoxyphenyl                                                          288                                                                               H  3-Phenoxyphenyl                                                          289                                                                               H  4-Phenoxyphenyl                                                          290                                                                               H  2-Benzyloxyphenyl                                                        291                                                                               H  3-Benzyloxyphenyl                                                        292                                                                               H  4-Benzyloxyphenyl m.p.: 94-96° C.                                 293                                                                               H  4-(Imidazol-1'-yl)phenyl                                                 294                                                                               H  4-(Piperazin-1'-yl)phenyl                                                295                                                                               H  4-(Morpholin-1'-yl)phenyl                                                296                                                                               H  4-(Piperidin-1'-yl)phenyl                                                297                                                                               H  4-(Pyridyl-2'-oxy)phenyl                                                 298                                                                               H  2-Cyclopropylphenyl                                                      299                                                                               H  3-Cyclopropylphenyl                                                      300                                                                               H  4-Cyclopropylphenyl                                                      301                                                                               H  3-Cyclohexylphenyl                                                       302                                                                               H  4-Cyclohexylphenyl                                                       303                                                                               H  4-Oxiranylphenyl                                                         304                                                                               H  4-(1',3'-Dioxan-2'-yl)phenyl                                             305                                                                               H  4-(Tetrahydropyran-2-yloxy)phenyl                                        306                                                                               H  1-Naphthyl                                                               307                                                                               H  2-Naphthyl        oil; IR (film): 1707,                                                          1633, 1257, 1129, 110                                  308                                                                               H  9-Anthryl                                                                309                                                                               H  1-Naphtoxy                                                               310                                                                               H  2-Naphtoxy                                                               311                                                                               H  9-Anthroxy                                                               312                                                                               H  Phenoxy                                                                  313                                                                               H  2-Chlorophenoxy                                                          314                                                                               H  3-Chlorophenoxy                                                          315                                                                               H  4-Chlorophenoxy                                                          316                                                                               H  4-Methylphenoxy                                                          317                                                                               H  4-tert.-Butylphenoxy                                                     318                                                                               H  4-Methoxyphenoxy                                                         319                                                                               H  4-Ethoxyphenoxy                                                          320                                                                               H  4-tert.-Butoxyphenoxy                                                    321                                                                               H  Phenylthio                                                               322                                                                               H  2-Chlorophenylthio                                                       323                                                                               H  4-Chlorophenylthio                                                       324                                                                               H  Benzyl                                                                   325                                                                               H  2-Methylbenzyl                                                           326                                                                               H  3-Methylbenzyl                                                           327                                                                               H  4-Methylbenyzl                                                           328                                                                               H  4-tert.-Butylbenzyl                                                      329                                                                               H  2-Chlorobenzyl                                                           330                                                                               H  3-Chlorobenzyl                                                           331                                                                               H  4-Chlorobenzyl                                                           332                                                                               H  2,4-Dichlorobenzyl                                                       333                                                                               H  2,6-Dichlorobenzyl                                                       334                                                                               H  2,4,6-Trichlorobenzyl                                                    335                                                                               H  2-Trifluoromethylbenzyl                                                  336                                                                               H  3-Trifluoromethylbenzyl                                                  337                                                                               H  4-Trifluoromethylbenzyl                                                  338                                                                               H  2-Methoxybenzyl                                                          339                                                                               H  4-Methoxybenzyl                                                          340                                                                               H  4-tert.-Butoxybenzyl                                                     341                                                                               H  4-Phenoxybenzyl                                                          342                                                                               H  1-Phenethyl                                                              343                                                                               H  2-Phenethyl                                                              344                                                                               H  1-Phenylpropyl                                                           345                                                                               H  2-Phenylpropyl                                                           346                                                                               H  3-Phenylpropyl                                                           347                                                                               H  2-Methyl-2-phenylpropyl                                                  348                                                                               H  2-Methyl-3-phenylpropyl                                                  349                                                                               H  4-Phenylbutyl                                                            350                                                                               H  2-Phenyl-1-ethenyl                                                       351                                                                               H  1-Phenyl-1-ethenyl                                                       352                                                                               H  1-Phenyl-1-propenyl                                                      353                                                                               H  1-Phenyl-1-propen-2-yl                                                   354                                                                               H  2,2-Diphenylethenyl                                                      355                                                                               H  Phenoxymethyl                                                            356                                                                               H  2-Pyridyl                                                                357                                                                               H  3-Pyridyl                                                                358                                                                               H  4-Pyridyl                                                                359                                                                               H  2,6-Pyrimidinyl                                                          360                                                                               H  1,5-Pyrimidinyl                                                          361                                                                               H  2-Thienyl                                                                362                                                                               H  3-Thienyl                                                                363                                                                               H  2-Furyl                                                                  364                                                                               H  3-Furyl                                                                  365                                                                               H  1-Pyrrolyl                                                               366                                                                               H  1-Imidazolyl                                                             367                                                                               H  1,2,4-Triazolyl                                                          368                                                                               H  1,3,4-Triazolyl                                                          369                                                                               H  4-Thiazolyl                                                              370                                                                               H  2-Benzothiazolyl                                                         371                                                                               H  2-Pyridyloxy                                                             372                                                                               H  2-Pyrimidinyloxy                                                         373                                                                               H  2-Pyridylthio                                                            374                                                                               H  2-Pyrimidinylthio                                                        375                                                                               H  2-Benzothiazolylthio                                                     376                                                                               H  Phenylthiomethyl                                                         377                                                                               H  2-Pyridylmethyl                                                          378                                                                               H  3-Pyridylmethyl                                                          379                                                                               H  Furfuryloxy                                                              380                                                                               H  Thienylmethoxy                                                           381                                                                               H  3-Isoxazolylmethoxy                                                      382                                                                               H  2-Oxazolylmethoxy                                                        383                                                                               H  2-Pyridylmethoxy                                                         384                                                                               H  2'-Furyl-2-ethenyl                                                       384                                                                               H  2'-Thienyl-2-ethenyl                                                     385                                                                               H  3'-Pyridyl-2-ethenyl                                                     386                                                                               H  Oxiranyl                                                                 388                                                                               H  1-Aziridinyl                                                             389                                                                               H  1-Azetidinyl                                                             390                                                                               H  1-Pyrrolidinyl                                                           391                                                                               H  2-Tetrahydrofuryl                                                        392                                                                               H  2-Tetrahydropyranyl                                                      393                                                                               H  3-Tetrahydropyranyl                                                      394                                                                               H  1-Piperidinyl                                                            395                                                                               H  1-Morpholinyl                                                            396                                                                               H  1-Piperazinyl                                                            397                                                                               H  1,3-Dioxan-2-yl                                                          398                                                                               H  3-Tetrahydrothiopyranyl                                                  399                                                                               H  2-Dihydropyranyloxy                                                      400                                                                               H  2-Tetrahydropyranyloxy                                                   401                                                                               H  CF.sub.3                                                                 402                                                                               H  2-Fluoroethyl                                                            403                                                                               H  2,2,2-Trifluoroethyl                                                     404                                                                               H  Pentafluoroethyl                                                         405                                                                               H  Chloromethyl                                                             406                                                                               H  Dichloromethyl                                                           407                                                                               H  Trichloromethyl                                                          408                                                                               H  2-Chloroethyl                                                            409                                                                               H  2,2,2-Trichloroethyl                                                     410                                                                               H  Pentachloroethyl                                                         411                                                                               H  Cyclopropyl                                                              412                                                                               H  Cyclobutyl                                                               413                                                                               H  Cyclopentyl                                                              414                                                                               H  Cyclohexyl                                                               415                                                                               H  1-Methylcyclopropyl                                                      416                                                                               H  2,2-Dimethylcyclopropyl                                                  417                                                                               H  1-Methylcyclohexyl                                                       418                                                                               H  2,2-Difluorocyclopropyl                                                  419                                                                               H  2,2-Dichlorocyclopropyl                                                  420                                                                               H  2,2-Dibromocyclopropyl                                                   421                                                                               H  2,2-Dichloro-3-Methylcyclopropyl                                         422                                                                               H  2,2,3,3-Tetrafluorocyclobutyl                                            423                                                                               H  Ethenyl                                                                  424                                                                               H  1-Propenyl                                                               425                                                                               H  2-Methyl-1-propenyl                                                      426                                                                               H  4-Methylpent-3-en-1-yl                                                   427                                                                               H  2-Propenyl                                                               428                                                                               H  2-Butenyl                                                                429                                                                               H  1-Methyl-2-propenyl                                                      430                                                                               H  3-Methyl-2-butenyl                                                       431                                                                               H  2,2-Difluoroethenyl                                                      432                                                                               H  2,2-Dichloroethenyl                                                      433                                                                               H  3,3,3-Trifluoropropenyl                                                  434                                                                               H  3,3,3-Trichloropropenyl                                                  435                                                                               H  3-Chloro-2-propenyl                                                      436                                                                               H  Cyclopent-1-enyl                                                         437                                                                               H  Cyclopentadienyl                                                         438                                                                               H  Cyclohex-1-enyl                                                          439                                                                               H  Pentafluorocyclopentadienyl                                              440                                                                               H  Pentachlorocyclopentadienyl                                              441                                                                               H  4-Dimethylaminophenyl                                                                            m.p.: 90-92° C.                                 442                                                                               H  4-n-Butoxyphenyl  m.p.: 79-82° C.                                 __________________________________________________________________________

                  TABLE VI                                                         ______________________________________                                          ##STR31##                                                                     No.  R.sub.3                                                                              R.sub.4              Data                                           ______________________________________                                          1   H     H                    m.p.: 94-95° C.                          2   H     Methoxymethyl                                                        3   H     Ethoxymethyl                                                         4   H     n-Propoxymethyl                                                      5   H     iso-Propoxymethyl                                                    6   H     tert.-Butoxymethyl                                                   7   H     2-Methoxyprop-2-yl                                                   8   H     2-Ethoxyprop-2-yl                                                    9   H     2-n-Propoxyprop-2-yl                                                 10  H     2-iso-Propoxyprop-2-yl                                               11  H     2-tert.-Butoxyprop-2-yl                                              12  H     Methylthiomethyl                                                     13  H     tert.-Butylthiomethyl                                                14  H     2-Methylthioprop-2-yl                                                15  H     2-iso-Propylthioprop-2-yl                                            16  H     2-tert.-Butylthioprop-2-yl                                           17  H     Methyl                                                               18  H     Ethyl                                                                19  H     n-Propyl                                                             20  H     iso-Propyl                                                           21  H     n-Butyl                                                              22  H     iso-Butyl                                                            23  H     sec.-Butyl                                                           24  H     tert.-Butyl                                                          25  H     n-Hexyl                                                              26  H     n-Decyl                                                              27  H     Cyclopropyl                                                          28  H     Cyclohexyl                                                           29  H     Phenylthiomethyl                                                     30  H     2-Phenylthiomethyl                                                   31  H     2-(2'-Chlorophenylthio)prop-2-yl                                     32  H     Ethynyl                                                              33  H     1-Propynyl                                                           34  H     Methoxy                                                              35  H     Ethoxy                                                               36  H     n-Propoxy                                                            37  H     iso-Propoxy                                                          38  H     n-Butoxy                                                             39  H     iso-Butoxy                                                           40  H     sec.-Butoxy                                                          41  H     tert.-Butoxy                                                         42  H     Methylthio                                                           43  H     Ethylthio                                                            44  H     n-Propylthio                                                         45  H     iso-Propylthio                                                       46  H     n-Butylthio                                                          47  H     iso-Butylthio                                                        48  H     sec.-Butylthio                                                       49  H     tert.-Butylthio                                                      50  H     Benzylthio                                                           51  H     Trifluoromethoxy                                                     52  H     Cyano                                                                53  H     Amino                                                                54  H     Methylamino                                                          55  H     Dimethylamino                                                        56  H     Ethylamino                                                           57  H     Diethylamino                                                         58  H     Di-n-Propylamino                                                     59  H     Di-iso-Propylamino                                                   60  H     Di-n-Butylamino                                                      61  H     Di-iso-Butylamino                                                    62  H     Acetyl                                                               63  H     Propion-1-yl                                                         64  H     Butyr-1-yl                                                           65  H     iso-Butyr-1-yl                                                       66  H     Pivaloyl                                                             67  H     Benzoyl                                                              68  H     4-Chlorobenzoyl                                                      69  H     Benzylcarbonyl                                                       70  H     Methoxycarbonyl                                                      71  H     Ethoxycarbonyl                                                       72  H     n-Propoxycarbonyl                                                    73  H     iso-Propoxycarbonyl                                                  74  H     n-Butoxycarbonyl                                                     75  H     iso-Butoxycarbonyl                                                   76  H     sec.-Butoxycarbonyl                                                  77  H     tert.-Butoxycarbonyl                                                 78  H     n-Hexoxycarbonyl                                                     79  H     PhenoxyCarbonyl                                                      80  H     4-Chlorophenoxycarbonyl                                              81  H     Benzyloxycarbonyl                                                    82  H     Aminocarbonyl                                                        83  H     Dimethylaminocarbonyl                                                84  H     Diethylaminocarbonyl                                                 85  H     Di-iso-Propylaminocarbonyl                                           86  H     Phenylaminocarbonyl                                                  87  H     N-Methyl-N-Phenylaminocarbonyl                                       88  H     Phenyl               m.p.: 92-95° C.                          89  H     2-Fluorophenyl       m.p.: 92-95° C.                          90  H     3-Fluorophenyl       m.p.: 58-60° C.                          91  H     4-Fluorophenyl       m.p.: 110-111° C.                        92  H     Pentafluorophenyl    m.p.: 118-120° C.                        93  H     2-Chlorophenyl       .sup.1 H-NMR                                                                   (CDCl.sub.3):                                                                  δ = 3.70s,                                                               3.82s, 5.15s,                                                                  7.15-7.40m,                                                                    7.52m, 7.60s,                                                                  7.85m, 8.52s                                    94  H     3-Chlorophenyl       m.p.: 58-60° C.                          95  H     4-Chlorophenyl       m.p.: 146-148° C.                        96  H     Pentachlorophenyl                                                    97  H     2,3-Dichlorophenyl   m.p.: 95-97° C.                          98  H     2,4-Dichlorophenyl   m.p.: 58-62° C.                          99  H     2,5-Dichlorophenyl                                                  100  H     2,6-Dichlorophenyl   m.p.: 136-140° C.                       101  H     3,4-Dichlorophenyl   m.p.: 94-97° C.                         102  H     3,5-Dichlorophenyl   m.p.: 88-91° C.                         103  H     2,3,4-Trichlorophenyl                                               104  H     2,3,5-Trichlorophenyl                                               105  H     2,3,6-Trichlorophenyl                                               106  H     2,4,5-Trichlorophenyl                                               107  H     2,4,6-Trichlorophenyl                                               108  H     3,4,5-Trichlorophenyl                                               109  H     2,3,4,6-Tetrachlorophenyl                                           110  H     2,3,5,6-Tetrachlorophenyl                                           111  H     2-Bromophenyl        m.p.: 91-94° C.                         112  H     3-Bromophenyl        m.p.: 63-64° C.                         113  H     4-Bromophenyl        m.p.: 145-147° C.                       114  H     2,4-Dibromophenyl                                                   115  H     3-Bromo-4-Fluorophenyl                                              116  H     3-Bromo-4-Methoxyphenyl                                             117  H     2-Iodophenyl                                                        118  H     3-Iodophenyl                                                        119  H     4-lodophenyl         m.p.: 90-93° C.                         120  H     2-Chloro-4-Fluorophenyl                                             121  H     2-Chloro-5-Fluorophenyl                                             122  H     2-Chloro-6-Fluorophenyl                                                                             m.p.: 111-113° C.                       123  H     2-Chloro-4-Bromophenyl                                              124  H     2-Bromo-4-Chlorophenyl                                              125  H     2-Bromo-4-Fluorophenyl                                              126  H     3-Bromo-4-Chlorophenyl                                              127  H     3-Chloro-4-Fluorophenyl                                             128  H     3-Fluoro-4-Chlorophenyl                                             129  H     2-Cyanophenyl                                                       130  H     3-Cyanophenyl                                                       131  H     4-Cyanophenyl                                                       132  H     2-Nitrophenyl                                                       133  H     3-Nitrophenyl                                                       134  H     4-Nitrophenyl        m.p.: 142-146° C.                       135  H     2-Methylphenyl       m.p.: 58-60° C.                         136  H     3-Methylphenyl       m.p.: 70-72° C.                         137  H     4-Methylphenyl       m.p.: 99-102° C.                        138  H     2,4-Dimethylphenyl   m.p.: 54-56° C.                         139  H     2,6-Dimethylphenyl                                                  140  H     3,4-Dimethylphenyl                                                  141  H     3,5-Dimethylphenyl                                                  142  H     2,3,4-Trimethylphenyl                                               143  H     2,3,5-Trimethylphenyl                                               144  H     2,3,6-Trimethylphenyl                                               145  H     2,4,5-Trimethylphenyl                                               146  H     2,4,6-Trimethylphenyl                                               147  H     3,4,5-Trimethylphenyl                                               148  H     Pentamethylphenyl                                                   149  H     2-Ethylphenyl                                                       150  H     3-Ethylphenyl                                                       151  H     4-Ethylphenyl                                                       152  H     3,5-Diethylphenyl                                                   153  H     2-n-Propylphenyl                                                    154  H     3-n-Propylphenyl                                                    155  H     4-n-Propylphenyl                                                    156  H     2-iso-Propylphenyl                                                  157  H     3-iso-Propylphenyl                                                  158  H     4-iso-Propylphenyl                                                  159  H     2,4-Di-iso-Propylphenyl                                             160  H     3,5-Di-iso-Propylphenyl                                             161  H     4-n-Butylphenyl                                                     162  H     4-sec.-Butylphenyl                                                  163  H     4-iso-Butylphenyl                                                   164  H     4-tert.-Butylphenyl  m.p.: 82-84° C.                         165  H     3-tert.-Butylphenyl                                                 166  H     2-tert.-Butylphenyl                                                 167  H     2,4-Di-tert.-Butylphenyl                                            168  H     3,5-Di-tert.-Butylphenyl                                            169  H     4-n-Hexylphenyl                                                     170  H     4-n-Dodecylphenyl                                                   171  H     2-Methyl-4-tert.-Butylphenyl                                        172  H     2-Methyl-6-tert.-Butylphenyl                                        173  H     2-Methyl-4-iso-Propylphenyl                                         174  H     2-Methyl-4-Cyclohexylphenyl                                         175  H     2-Methyl-4-Phenylphenyl                                             176  H     2-Methyl-4-Benzylphenyl                                             177  H     2-Methyl-4-Phenoxyphenyl                                            178  H     2-Methyl-4-Benzyloxyphenyl                                          179  H     2-Methyl-3-Chlorophenyl                                             180  H     2-Methyl-4-Chlorophenyl                                             181  H     2-Methyl-5-Chlorophenyl                                             182  H     2-Methyl-6-Chlorophenyl                                             183  H     2-Methyl-4-Fluorophenyl                                             184  H     2-Methyl-3-Bromophenyl                                              185  H     2-Methyl-4-Bromophenyl                                              186  H     2-Methyl-3-methoxyphenyl                                            187  H     2-Methyl-4-methoxyphenyl                                            188  H     2-Methyl-5-Methoxyphenyl                                            189  H     2-Methyl-6-Methoxyphenyl                                            190  H     2-Methyl-4-iso-Propoxyphenyl                                        191  H     2-Methyl-2,5-Dimethoxyphenyl                                        192  H     2-Methoxyphenyl      m.p.: 65-68° C.                         193  H     3-Methoxyphenyl      m.p.: 83-84° C.                         194  H     4-Methoxyphenyl      m.p.: 88-90° C.                         195  H     2,3-Dimethoxyphenyl                                                 196  H     2,4-Dimethoxyphenyl  m.p.: 90-93° C.                         197  H     2,5-Dimethoxyphenyl                                                 198  H     2,6-Dimethoxyphenyl                                                 199  H     3,4-Dimethoxyphenyl  m.p.: 70-72° C.                         200  H     3,5-Dimethoxyphenyl  m.p.: 97-99° C.                         201  H     3,6-Dimethoxyphenyl                                                 202  H     2,3,4-Trimethoxyphenyl                                              203  H     2,3,5-Trimethoxyphenyl                                              204  H     2,3,6-Trimethoxyphenyl                                              205  H     2,4,5-Trimethoxyphenyl                                              206  H     2,4,6-Trimethoxyphenyl                                              207  H     3,4,5-Trimethoxyphenyl                                                                              m.p.: 105-109° C.                       208  H     2-Ethoxyphenyl                                                      209  H     3-Ethoxyphenyl       m.p.: 90-92° C.                         210  H     4-Ethoxyphenyl       m.p.: 97-98° C.                         211  H     2-iso-Propoxyphenyl                                                 212  H     3-iso-Propoxyphenyl                                                 213  H     4-iso-Propoxyphenyl                                                 214  H     3-tert.-Butoxyphenyl                                                215  H     4-tert.-Butoxyphenyl m.p.: 78-83° C.                         216  H     2-Trifluoromethoxyphenyl                                            217  H     3-Trifluoromethoxyphenyl                                            218  H     4-Trifluoromethoxyphenyl                                            219  H     3-(1',1',2',2'-Tetrafluoro)ethoxy-                                             phenyl                                                              220  H     4-(1',1',2',2'-Tetrafluoro)ethoxy-                                             phenyl                                                              221  H     2-Chloromethylphenyl                                                222  H     3-Chloromethylphenyl                                                223  H     4-Chloromethylphenyl                                                224  H     2-Trifluoromethylphenyl                                                                             m.p.: 58-60° C.                         225  H     3-Trifluoromethylphenyl                                                                             m.p.: 74-77° C.                         226  H     4-Trifluoromethylphenyl                                                                             m.p.: 120-122° C.                       227  H     2-(Methoxyiminomethyl)phenyl                                        228  H     3-(Methoxyiminomethyl)phenyl                                        229  H     4-(Methoxyiminomethyl)phenyl                                        230  H     2-(Ethoxyiminomethyl)phenyl                                         231  H     3-(Ethoxyiminomethyl)phenyl                                         232  H     4-(Ethoxyiminomethyl)phenyl                                         233  H     2-(n-Propoxyiminomethyl)phenyl                                      234  H     3-(n-Propoxyiminomethyl)phenyl                                      235  H     4-(n-Propoxyiminomethyl)phenyl                                      236  H     2-(iso-Propoxyiminomethyl)phenyl                                    237  H     3-(iso-Propoxyiminomethyl)phenyl                                    238  H     4-(iso-Propoxyiminomethyl)phenyl                                    239  H     2-(n-Butoxyiminomethyl)phenyl                                       240  H     3-(n-Butoxyiminomethyl)phenyl                                       241  H     4-(n-Butoxyiminomethyl)phenyl                                       242  H     2-(iso-Butoxyiminomethyl)phenyl                                     243  H     3-(iso-Butoxyiminomethyl)phenyl                                     244  H     4-(iso-Butoxyiminomethyl)phenyl                                     245  H     2-(tert.-Butoxyiminomethyl)phenyl                                   246  H     3-(tert.-Butoxyiminomethyl)phenyl                                   247  H     4-(tert.-Butoxyiminomethyl)phenyl                                   248  H     2-(n-Pentoxyiminomethyl)phenyl                                      249  H     3-(n-Pentoxyiminomethyl)phenyl                                      250  H     4-(n-Pentoxyiminomethyl)phenyl                                      251  H     2-(n-Hexoxyiminomethyl)phenyl                                       252  H     3-(n-Hexoxyiminomethyl)phenyl                                       253  H     4-(n-Hexoxyiminomethyl)phenyl                                       254  H     2-(Allyloxyiminomethyl)phenyl                                       255  H     3-(Allyloxyiminomethyl)phenyl                                       256  H     4-(Allyloxyiminomethyl)phenyl                                       257  H     2-(Benzyloxyiminomethyl)phenyl                                      258  H     3-(Benzyloxyiminomethyl)phenyl                                      259  H     4-(Benzyloxyiminomethyl)phenyl                                      260  H     2-(Methoxyimino-1'-ethyl)phenyl                                     261  H     3-(Methoxyimino-1'-ethyl)phenyl                                     262  H     4-(Methoxyimino-1'-ethyl)phenyl                                     263  H     2-(Ethoxyimino-1'-ethyl)phenyl                                      264  H     3-(Ethoxyimino-1'-ethyl)phenyl                                      265  H     4-(Ethoxyimino-1'-ethyl)phenyl                                      266  H     2-(n-Propoxyimino-1'-ethyl)phenyl                                   267  H     3-(n-Propoxyimino-1'-ethyl)phenyl                                   268  H     4-(n-Propoxyimino-1'-ethyl)phenyl                                   269  H     2-(n-Butoxyamino-1'-ethyl)phenyl                                    270  H     3-(n-Butoxyamino-1'-ethyl)phenyl                                    271  H     4-(n-Butoxyamino-1'-ethyl)phenyl                                    272  H     2-(n-Pentoxyimino-1'-ethyl)phenyl                                   273  H     3-(n-Pentoxyimino-1'-ethyl)phenyl                                   274  H     4-(n-Pentoxyimino-1'-ethyl)phenyl                                   275  H     2-(n-Hexoxyimino-1'-ethyl)phenyl                                    276  H     3-(n-Hexoxyimino-1'-ethyl)phenyl                                    277  H     4-(n-Hexoxyimino-1'-ethyl)phenyl                                    278  H     2-(Allyloxyimino-1'-ethyl)phenyl                                    279  H     3-(Allyloxyimino-1'-ethyl)phenyl                                    280  H     4-(Allyloxyimino-1'-ethyl)phenyl                                    281  H     2-(Benzyloxyimino-1'-ethyl)phenyl                                   282  H     3-(Benzyloxyimino-1'-ethyl)phenyl                                   283  H     4-(Benzyloxyimino-1'-ethyl)phenyl                                   284  H     2-Phenylphenyl                                                      285  H     3-Phenylphenyl                                                      286  H     4-Phenylphenyl       m.p.: 100-102° C.                       287  H     2-Phenoxyphenyl                                                     288  H     3-Phenoxyphenyl      IR (film): 1728,                                                               1489, 1247, 1214,                                                              1070, 1020                                     289  H     4-Phenoxyphenyl      m.p.: 85-87° C.                         290  H     2-Benzyloxyphenyl    m.p.: 83-85° C.                         291  H     3-Benzyloxyphenyl    m.p.: 66-68° C.                         292  H     4-Benzyloxyphenyl    m.p.: 104-106° C.                       293  H     4-(Imidazol-1'-yl)phenyl                                            294  H     4-(Piperazin-1'-yl)phenyl                                           295  H     4-(Morpholin-1'-yl)phenyl                                           296  H     4-(Piperidin-1'-yl)phenyl                                           297  H     4-(Pyridyl-2'-oxy)phenyl                                            298  H     2-Cyclopropylphenyl                                                 299  H     3-Cyclopropylphenyl                                                 300  H     4-Cyclopropylphenyl                                                 301  H     3-Cyclohexylphenyl                                                  302  H     4-Cyclohexylphenyl                                                  303  H     4-Oxiranylphenyl                                                    304  H     4-(1',3'-Dioxan-2'-yl)phenyl                                        305  H     4-(Tetrahydropyran-2-yloxy)phenyl                                   306  H     1-Naphthyl           m.p.: 70-73° C.                         307  H     2-Naphthyl           m.p.: 125-126° C.                       308  H     9-Anthryl                                                           309  H     1-Naphthoxy                                                         310  H     2-Naphthoxy                                                         311  H     9-Anthroxy                                                          312  H     Phenoxy                                                             313  H     2-Chlorophenoxy                                                     314  H     3-Chlorophenoxy                                                     315  H     4-Chlorophenoxy                                                     316  H     4-Methylphenoxy                                                     317  H     4-tert.-Butylphenoxy                                                318  H     4-Methoxyphenoxy                                                    319  H     4-Ethoxyphenoxy                                                     320  H     4-tert.-Butoxyphenoxy                                               321  H     Phenylthio                                                          322  H     2-Chlorophenylthio                                                  323  H     4-Chlorophenylthio                                                  324  H     Benzyl                                                              325  H     2-Methylbenzyl                                                      326  H     3-Methylbenzyl                                                      327  H     4-Methylbenyzl                                                      328  H     4-tert.-Butylbenzyl                                                 329  H     2-Chlorobenzyl                                                      330  H     3-Chlorobenzyl                                                      331  H     4-Chlorobenzyl                                                      332  H     2,4-Dichlorobenzyl                                                  333  H     2,6-Dichlorobenzyl                                                  334  H     2,4,6-Trichlorobenzyl                                               335  H     2-Trifluoromethylbenzyl                                             336  H     3-Trifluoromethylbenzyl                                             337  H     4-Trifluoromethylbenzyl                                             338  H     2-Methoxybenzyl                                                     339  H     4-Methoxybenzyl                                                     340  H     4-tert.-Butoxybenzyl                                                341  H     4-Phenoxybenzyl                                                     342  H     1-Phenethyl                                                         343  H     2-Phenethyl                                                         344  H     1-Phenylpropyl                                                      345  H     2-Phenylpropyl                                                      346  H     3-Phenylpropyl                                                      347  H     2-Methyl-2-phenylpropyl                                             348  H     2-Methyl-3-phenylpropyl                                             349  H     4-Phenylbutyl                                                       350  H     2-Phenyl-1-ethenyl                                                  351  H     1-Phenyl-1-ethenyl                                                  352  H     1-Phenyl-1-propenyl                                                 353  H     1-Phenyl-1-propen-2-yl                                              354  H     2,2-Diphenylethenyl                                                 355  H     Phenoxymethyl                                                       356  H     2-Pyridyl                                                           357  H     3-Pyridyl                                                           358  H     4-Pyridyl                                                           359  H     2,6-Pyrimidinyl                                                     360  H     1,5-Pyrimidinyl                                                     361  H     2-Thienyl                                                           362  H     3-Thienyl                                                           363  H     2-Furyl                                                             364  H     3-Furyl                                                             365  H     1-Pyrrolyl                                                          366  H     1-Imidazolyl                                                        367  H     1,2,4-Triazolyl                                                     368  H     1,3,4-Triazolyl                                                     369  H     4-Thiazolyl                                                         370  H     2-Benzothiazolyl                                                    371  H     2-Pyridyloxy                                                        372  H     2-Pyrimidinyloxy                                                    373  H     2-Pyridylthio                                                       374  H     2-Pyrimidinylthio                                                   375  H     2-Benzothiazolylthio                                                376  H     Phenylthiomethyl                                                    377  H     2-Pyridylmethyl                                                     378  H     3-Pyridylmethyl                                                     379  H     Furfuryloxy                                                         380  H     Thienylmethoxy                                                      381  H     3-Isoxazolylmethoxy                                                 382  H     2-Oxazolylmethoxy                                                   383  H     2-Pyridylmethoxy                                                    384  H     2'-Furyl-2-ethenyl                                                  385  H     2'-Thienyl-2-ethenyl                                                386  H     3'-Pyridyl-2-ethenyl                                                387  H     Oxiranyl                                                            388  H     1-Aziridinyl                                                        389  H     1-Azetidinyl                                                        390  H     1-Pyrrolidinyl                                                      391  H     2-Tetrahydrofuryl                                                   392  H     2-Tetrahydropyranyl                                                 393  H     3-Tetrahydropyranyl                                                 394  H     1-Piperidinyl                                                       395  H     1-Morpholinyl                                                       396  H     1-Piperazinyl                                                       397  H     1,3-Dioxan-2-yl                                                     398  H     3-Tetrahydrothiopyranyl                                             399  H     2-Dihydropyranyloxy                                                 400  H     2-Tetrahydropyranyloxy                                              401  H     CF.sub.3                                                            402  H     2-Fluoroethyl                                                       403  H     2,2,2-Trifluoroethyl                                                404  H     Pentafluoroethyl                                                    405  H     Chloromethyl                                                        406  H     Dichloromethyl                                                      407  H     Trichloromethyl                                                     408  H     2-Chloroethyl                                                       409  H     2,2,2-Trichloroethyl                                                410  H     Pentachloroethyl                                                    411  H     Cyclopropyl                                                         412  H     Cyclobutyl                                                          413  H     Cyclopentyl                                                         414  H     Cyclohexyl                                                          415  H     1-Methylcyclopropyl                                                 416  H     2,2-Dimethylcyclopropyl                                             417  H     1-Methylcyclohexyl                                                  418  H     2,2-Difluorocyclopropyl                                             419  H     2,2-Dichlorocyclopropyl                                             420  H     2,2-Dibromocyclopropyl                                              421  H     2,2-Dichloro-3-methylcyclopropyl                                    422  H     2,2,3,3-Tetrafluorocyclobutyl                                       423  H     Ethenyl                                                             424  H     1-Propenyl                                                          425  H     2-Methyl-1-propenyl                                                 426  H     4-Methylpent-3-en-1-yl                                              427  H     2-Propenyl                                                          428  H     2-Butenyl                                                           429  H     1-Methyl-2-propenyl                                                 430  H     3-Methyl-2-butenyl                                                  431  H     2,2-Difluoroethenyl                                                 432  H     2,2-Dichloroethenyl                                                 433  H     3,3,3-Trifluoropropenyl                                             434  H     3,3,3-Trichloropropenyl                                             435  H     3-Chloro-2-propenyl                                                 436  H     Cyclopent-1-enyl                                                    437  H     Cyclopentadienyl                                                    438  H     Cyclohex-1-enyl                                                     439  H     Pentafluorocyclopentadienyl                                         440  H     Pentachlorocyclopentadienyl                                         441  H     4-Dimethylaminophenyl                                                                               m.p.: 70-71° C.                         442  H     4-Allyloxyphenyl     m.p.: 81-83° C.                         443  H     Diphenylmethyl       m.p.: 66-68° C.                         444  H     Dimethylbenzyl       .sup.1 H-NMR                                                                   (CDCl.sub.3):                                                                  δ = 1.45s                                                                3.78s, 4.03s, 5.00s                                                            7.17-7.41m                                     ______________________________________                                    

                  TABLE VII                                                        ______________________________________                                          ##STR32##                                                                     No.      R.sup.8.sub.n Data                                                    ______________________________________                                          1       H             m.p. 156-158° C.                                  2       3-Fluoro                                                               3       4-Fluoro                                                               4       3-Chloro                                                               5       4-Chloro                                                               6       3-Bromo                                                                7       4-Bromo                                                                8       3-Iodo                                                                 9       4-Iodo                                                                10       3,4-Dichloro                                                          11       3,5-Dichloro                                                          12       3,6-Dichloro                                                          13       4,5-Dichloro                                                          14       3,4,5-Trichloro                                                       15       3,4,6-Trichloro                                                       16       3,4,5,6-Tetrachloro                                                   17       3,4,5,6-Tetrafluoro                                                   18       3,4,5,6-Tetrabromo                                                    19       3,5-Difluoro                                                          20       3,5-Dibromo                                                           21       3-Methyl                                                              22       4-Methyl                                                              23       3-Ethyl                                                               24       4-Ethyl                                                               25       3-iso-Propyl                                                          26       4-iso-Propyl                                                          27       3-tert-Butyl                                                          28       4-tert-Butyl                                                          29       3,4-Dimethyl                                                          30       3,5-Dimethyl                                                          31       3,6-Dimethyl                                                          32       4,5-Dimethyl                                                          33       3,4,5-Trimethyl                                                       34       3,4,6-Trimethyl                                                       35       3,4,5,6-Tetramethyl                                                   36       3-Nitro                                                               37       4-Nitro                                                               38       3,5-Dinitro                                                           39       3-Cyano                                                               40       4-Cyano                                                               41       3-Methoxy                                                             42       4-Methoxy                                                             43       3-tert.Butoxy                                                         44       4-tert.Butoxy                                                         45       3-Trifluoromethyl                                                     46       4-Trifluoromethyl                                                     47       3-Chloromethyl                                                        48       4-Chloromethyl                                                        49       3-Trifluoromethoxy                                                    50       4-Trifluoromethoxy                                                    51       3-Benzyloxy                                                           52       4-Benzyloxy                                                           53       4,5-Dibenzyloxy                                                       54       3-Phenoxy                                                             55       4-Phenoxy                                                             56       3-Phenyl                                                              57       4-Phenyl                                                              58       3-Pyrid-2'-yl                                                         59       4-Pyrid-2'-yl                                                         60       3-Pyrid-2'-yloxy                                                      61       4-Pyrid-2'-yloxy                                                      ______________________________________                                    

                  TABLE VIII                                                       ______________________________________                                          ##STR33##                                                                     No.      R.sup.8.sub.n Data                                                    ______________________________________                                          1       H             m.p. 152-155° C.                                  2       3-Fluoro                                                               3       4-Fluoro                                                               4       3-Chloro                                                               5       4-Chloro                                                               6       3-Bromo                                                                7       4-Bromo                                                                8       3-Iodo                                                                 9       4-Iodo                                                                10       3,4-Dichloro                                                          11       3,5-Dichloro                                                          12       3,6-Dichloro                                                          13       4,5-Dichloro                                                          14       3,4,5-Trichloro                                                       15       3,4,6-Trichloro                                                       16       3,4,5,6-Tetrachloro                                                   17       3,4,5,6-Tetrafluoro                                                   18       3,4,5,6-Tetrabromo                                                    19       3,5-Difluoro                                                          20       3,5-Dibromo                                                           21       3-Methyl                                                              22       4-Methyl                                                              23       3-Ethyl                                                               24       4-Ethyl                                                               25       3-iso-Propyl                                                          26       4-iso-Propyl                                                          27       3-tert-Butyl                                                          28       4-tert-Butyl                                                          29       3,4-Dimethyl                                                          30       3,5-Dimethyl                                                          31       3,6-Dimethyl                                                          32       4,5-Dimethyl                                                          33       3,4,5-Trimethyl                                                       34       3,4,6-Trimethyl                                                       35       3,4,5,6-Tetramethyl                                                   36       3-Nitro                                                               37       4-Nitro                                                               38       3,5-Dinitro                                                           39       3-Cyano                                                               40       4-Cyano                                                               41       3-Methoxy                                                             42       4-Methoxy                                                             43       3-tert.Butoxy                                                         44       4-tert.Butoxy                                                         45       3-Trifluoromethyl                                                     46       4-Trifluoromethyl                                                     47       3-Chloromethyl                                                        48       4-Chloromethyl                                                        49       3-Trifluoromethoxy                                                    50       4-Trifluoromethoxy                                                    51       3-Benzyloxy                                                           52       4-Benzyloxy                                                           53       4,5-Dibenzyloxy                                                       54       3-Phenoxy                                                             55       4-Phenoxy                                                             56       3-Phenyl                                                              57       4-Phenyl                                                              58       3-Pyrid-2'-yl                                                         59       4-Pyrid-2'-yl                                                         60       3-Pyrid-2'-yloxy                                                      61       4-Pyrid-2'-yloxy                                                      ______________________________________                                    

                  TABLE IX                                                         ______________________________________                                          ##STR34##                                                                     No.  X            Y      R.sup.1                                                                               R.sup.8 Data                                   ______________________________________                                          1   CHSCH.sub.3  O      CH.sub.3                                                                              H                                               2   CHSCH.sub.3  NH     CH.sub.3                                                                              H                                               3   CHSCH.sub.3  S      CH.sub.3                                                                              H                                               4   CH.sub.2     O      CH.sub.3                                                                              H                                               5   CH.sub.2     NH     CH.sub.3                                                                              H                                               6   CH.sub.2     S      CH.sub.3                                                                              H                                               7   CHCH.sub.3   O      CH.sub.3                                                                              H                                               8   CHCH.sub.3   NH     CH.sub.3                                                                              H                                               9   CHCH.sub.3   S      CH.sub.3                                                                              H                                              10   CHCH.sub.3   O      CH.sub.3                                                                              Perchloro                                      11   CHCH.sub.3   NH     CH.sub.3                                                                              Perchloro                                      12   CHCH.sub.3   S      CH.sub.3                                                                              Perchloro                                      13   CHOCH.sub.3  NH     CH.sub.3                                                                              H                                              14   CHOCH.sub.3  S      CH.sub.3                                                                              H                                              15   CHOCH.sub.3  NH     CH.sub.3                                                                              Perchloro                                      16   CHOCH.sub.3  S      CH.sub.3                                                                              Perchloro                                      17   NOCH.sub.3   NH     CH.sub.3                                                                              H                                              18   NOCH.sub.3   S      CH.sub.3                                                                              H                                              19   NOCH.sub.3   NH     CH.sub.3                                                                              Perchloro                                      20   NOCH.sub.3   S      CH.sub.3                                                                              Perchloro                                      ______________________________________                                    

In general terms, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes. Some of them have a systemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling the following plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia solani in cotton,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in fruit and vegetables.

The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. Either the fungi themselves, or the plants, seed or materials to be protected against fungus attack, or the soil are treated with a fungicidally effective amount of the active ingredient.

The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in Known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as ligninsulfite waste liquors and methylcellulose.

The fungicides generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt% of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials, e.g., on Paecilomyces variotii. When the active ingredients are used for treating seed, amounts of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally required.

The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. A solution of 90 parts by weight of compound no. 429 (Table I) and 10 parts by weight of N-methyl-α-pyrrolidone, which is suitable for application in the form of very fine drops.

II. A mixture of 20 parts by weight of compound no. 14 (Table II), 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.

III. An aqueous dispersion of 20 parts by weight of compound no. 49 (Table I), 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the solution in water, an aqueous dispersion is obtained.

IV. An aqueous dispersion of 20 parts by weight of compound no. 56 (Table I), 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely distributing the solution in water, an aqueous dispersion is obtained.

V. A hammer-milled mixture of 80 parts by weight of compound no. 14 (Table I), 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.

VI. An intimate mixture of 3 parts by weight of compound no. 17 (Table II) and 97 parts by weight of particulate Kaolin. The dust contains 3wt% of the active ingredient.

VII. An intimate mixture of 30 parts by weight of compound no. 17 (Table I), 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence.

VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 571 (Table I), 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts by weight of water, which dispersion can be further diluted.

IX. A stable oily dispersion of 20 parts by weight of compound no. 616 (Table I), 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.

In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in a greater fungicidal action spectrum.

Use examples

The active ingredient used for comparison purposes was 2-(phenoxymethyl)phenylglyoxylic acid-methyl ester-O-methyloxime (A) disclosed in EP 253,213.

Use Example 1 Action on wheat brown rust

Leaves of pot-grown wheat seedlings of the "Kanzler" variety were dusted with spores of brown rust (Puccinia recondita). The pots were then placed for 24 hours at 20° to 22° C. in a high-humidity (90-95%) chamber. During this period the spores germinated and the germ tubes penetrated the leaf tissue. The infected plants were then sprayed to runoff with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the plants were set up in the greenhouse at 20° to 22° C. and a relative humidity of 65 to 70%. The extent of rust fungus spread on the leaves was assessed after 8 days.

The results show that active ingredients nos. 49, 429, 56, 14, 15, 16, 17, 582, 578, 573, 592, 571, 704, 705 and 616 from Table I and nos. 17 and 644 from Table II, applied as 0.025wt% spray liquors, have a better fungicidal action (95%) than prior art comparative compound A (50%).

Use Example 2 Action on Pyricularia oryzae (protective)

Leaves of pot-grown rice seedlings of the "Bahia" variety were sprayed to runoff with aqueous emulsions containing (dry basis) 80% of active ingredient and 20% of emulsifier, and inoculated 24 hours later with an aqueous spore suspension of Pyricularia oryzae. The plants were then set up in climatic cabinets at 22° to 24° C. and 95 to 99% relative humidity. The extent of fungus attack was assessed after 6 days.

The results show that active ingredients nos. 429, 583, 593, 592, 571, 706 and 616 from Table I and nos. 14, 15, 16, 17, 582, 592, 571, 769, 782, 672, 644 and 583 from Table II, applied as 0.05wt% spray liquors, have a very good fungicidal action (100%).

The novel compounds are also suitable for effectively combating pests such as insects, arachnids and nematodes. They may be used as pesticides in crop protection and in the hygiene, stores protection and veterinary sector.

Examples of injurious insects belonging to the Lepidoptera order are Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerKella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scarbra, Plutella xylostella, Pseudoplusia includens, Phyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerelella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortfix viridana, Trichoplusia ni and Zeiraphera canadensis.

Examples from the Coleoptera order are Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Onlema oryzae, Ortiorrhynchus sulcatus, Ortiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria.

Examples from the Diptera order are Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa.

Examples from the Thysanoptera order are Franklinleila fusca, FranKliniella occidentalis, FranKliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci.

Examples from the Hymenoptera order are Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta.

Examples from the Heteroptera order are Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor.

Examples from the nematodes class are root-knot nematodes, e.g., Meloidogyne hapla, Meloidogyne incognita and Meloidogyne javanica, cyst-forming nematodes, e.g., Globodera rostochiensis, Heterodera avenae, Hetrodera glycinae, Heterodera schachtii and Heterodera trifolii, and stem and leaf eelworms, e.g., Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratytenchus goodeyi.

When the active ingredients are used for combating pests, the concentrations in the finished formulations may vary over a wide range. Generally, the concentration is from 0.0001 to 10, and preferably from 0.001 to 0.1%.

The active ingredients may also be successfully used in the ultra-low-volume method (ULV), where it is possible to apply formulations containing more than 95wt% of active ingredient, or even the active ingredient without any additives.

When the active ingredients are used for combating pests in the open, the application rates are from 0.01 to 10, and preferably from 0.1 to 1.0, kg/ha.

Example 3

Tetranychus telarius (spider mite); contact action--spray test

Potted bush beans which had developed the first pair of true leaves and were heavily infested with all stages of the spider mite Tetranychus telarius were sprayed to runoff in a spray cabinet with aqueous formulations of the active ingredients. The plants were placed on a rotating disc and sprayed from all sides with 50 ml of spray liquor. The plants were heavily infested with mites and numerous eggs had been laid on them. The action was assessed after 5 days by means of a binocular microscope. During this period, the plants were Kept under normal greenhouse conditions.

    ______________________________________                                                     Application rate                                                                         Mortality                                                            in ppm    in %                                                     ______________________________________                                         Compound no.                                                                   from Table I                                                                    49            100         80                                                   36            100         80                                                   43           1000        100                                                  429           1000        100                                                   38            40         100                                                   39            100        100                                                   45           1000        100                                                  582           about 2     100                                                  579            20          80                                                  583            40         100                                                  573            20         100                                                  593           1000         80                                                  592            40         100                                                  704           about 20    100                                                  705            40         100                                                  Compound no.                                                                   from Table II                                                                   37           1000        100                                                   39           1000        100                                                   45           1000        100                                                  ______________________________________                                    

Use Example 4

Musca domestica (housefly); continuous contact action

Both the tops and bottoms of Petri dishes 10 cm in diameter were lined with a total of 1 ml of acetonic solutions of the active ingredients. After the solvent had evaporated (about 30 mins.), 10 flies and absorbent cotton steeped in water were introduced into each dish and the dishes closed. The flies in supine position were counted after 24 hours.

If a kill rate of 80 to 100% occurs at a concentration of 0.01 mg/dish, the test is continued with falling concentrations.

    ______________________________________                                         Compound no.  Application rate                                                                           Mortality                                            from Table I  in mg       in %                                                 ______________________________________                                          49           0.1         80                                                    36           1.0         80                                                    37           0.1         100                                                  582           0.1         80                                                   593           0.1         60                                                   705           0.1         100                                                  706           0.1         100                                                  ______________________________________                                    

Use Example 5

Plutella maculipennis (diamondback moth); ingestion-inhibiting action Young kohlrabi leaves are dipped for 3 seconds into aqueous solutions of the candidate compounds, and then placed on a round filter paper 9 cm in diameter which has been moistened with 0.5 ml of water. The filter paper is then placed in a Petri dish 10 cm in diameter. 10 caterpillars in the 4th larval stage are then placed on each leaf, and the Petri dish is closed. Ingestion inhibition is determined in % after 48 hours.

    ______________________________________                                         Compound no.  Application rate                                                                           Mortality                                            from Table I  in ppm      in %                                                 ______________________________________                                          49           200         80                                                    36           200         80                                                   429           1000        80                                                    16           400         80                                                   582           400         100                                                  593           1000        80                                                   592           400         80                                                   705           400         80                                                   706           400         80                                                   ______________________________________                                    

Use Example 6

Action on Peronospora in grapes

Leaves of potted vines of the "MPUller Thurgau" variety were sprayed with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. To assess the duration of action of the active ingredients, the plants were, after the sprayed-on layer had dried, set up in the greenhouse for 8 days. Only then were the leaves infected with a zoospore suspension of Plasmopara viticola. The vines were then placed for 48 hours in a water-vapor-saturated chamber at 24° C. and then for 5 days in a greenhouse at from 20° to 30° C. To accelerate the sporangiophore discharge, the plants were then again set up in the moist chamber for 16 hours. The extent to which the leaves had been attacked was then assessed. The results show that active ingredients nos. 49, 429, 56, 14, 15, 16, 17, 582, 578, 573, 592, 571, 704, 705, 616, 117, 156, 579, 583, 593 and 706 from Table I, nos. 17, 644, 117, 429, 56, 43, 36, 49, 14, 15, 16, 582, 614 and 672 from Table II, and compound no. 1 from Table VII have, when applied as 0.025wt% spray liquors, a better fungicidal action (95%) than the prior art comparative agent A (50%). 

We claim:
 1. A compound of the formula I ##STR35## where X isCH--C₁ -C₄ -alkyl, Y is O, S or NR⁵, R¹, R² and R⁵ are H or C₁ -C₄ -alkyl, Z¹ and Z² are identical or different and each is H, halogen, methyl, methoxy or cyano, R³ and R⁴ are identical or different and each is hydrogen, Cyano, straight-chain or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₅ -haloalkenyl, C₃ -C₆ -cycloalkenyl, C₃ -C₆ -halocycloalkenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₄ -alkylthio, benzylthio, C₁ -C₄ -alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C₁ -C₄ -alkoxylcarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁ -C₄ -alkyl, substituted or unsubstituted aryl-C₂ -C₄ -alkenyl, substituted or unsubstituted aryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted arylthio-C₁ -C₄ -alkyl N(R⁶) where the radicals R⁶ are identical or different and each is H, C₁ -C₆ -alkyl or substituted or unsubstituted phenyl, --CO--N(R⁷)₂, where the radicals R⁷ are identical or different and each is H or C₁ -C₄ -alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₁₀ -alkoximino-C₁ -C₂ -alkyl, aryl, aryloxy, benzyloxy, or C₃ -C₆ -cycloalkyl, or R³ and R⁴ together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted, or R³ and R⁴ may be halogen, and "aryl" alone or as part of another radical, is phenyl, naphthyl or anthryl.
 2. A compound according to claim 1 wherein Z¹, Z² and R² are hydrogen; X is CH--CH³ ; Y is O, R¹ is methyl; R³ is selected from the group consisting of trifluoromethyl, cyclopropyl, cyano, methyl, isobutyl, phenyl, and hydrogen, and R⁴ is selected from the group consisting of phenyl, 4-chlorophenyl, 4-methoxyphenyl, 4-tert.-butylphenyl, methylthio, 2-methoxyprop-2-yl, 2-methylthioprop-2-yl, phenylthio, isopropyl, cyano, acetyl, benzoyl, methoxycarbonyl, 2-chlorophenyl, 2-methylphenyl, 4-(n-butoxyiminomethyl)phenyl, styryl, 1-propenyl, benzyl, tert.-butyl, 2-methylbutyl, isobutyl, naphthyl, 2-ethoxyprop-2-yl, 2-i-propoxyprop-2-yl, 2-n-butoxyprop-2-yl, 2-i-butoxyprop-2-yl, 2-ethylthioprop-2-yl, and 2-i-propylthioprop-2-yl, and wherein R³ together with R⁴ forms tetramethylene or pentamethylene.
 3. A compound according to claim 2 wherein R³ is cyano and R⁴ is selected from the group consisting of2-methoxyprop-2-yl, 2-methylthioprop-2-yl, isopropyl, phenyl, 2-ethoxyprop-2-yl, 2-i-propoxyprop-2-yl, 2-n-butoxyprop-2-yl, 2-i-butoxyprop-2-yl, cyclopropyl, 2-ethylthioprop-2-yl, and 2-i-propylthioprop-2-yl.
 4. A compound according to claim 2 wherein R³ is methyl and R⁴ is 4-chlorophenyl.
 5. A fungicidal composition containing an inert carrier and a fungicidally effective amount of an O-benzyloxime ether of the formula I ##STR36## where X is CH--C₁ -C₄ -alkyl,Y is O, S or NR⁵, R¹, R² and R⁵ are H or C₁ -C₄ -alkyl, Z¹ and Z² are identical or different and each is H, halogen, methyl, methoxy or cyano, R³ and R⁴ are identical or different and each is hydrogen, cyano, straight-chain or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₅ -haloalkenyl, C₃ -C₆ -cycloalkenyl, C₃ -C₆ -halocycloalkenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₄ -alkylthio, benzylthio, C₁ -C₄ -alkylcarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzylcarbonyl, C₁ -C₄ -alkoxylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁ -C₄ -alkyl, substituted or unsubstituted aryl-C₂ -C₄ -alkenyl, substituted or unsubstituted aryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted arylthio-C₁ -C₄ -alkyl, N(R⁶)₂, where the radicals R⁶ are identical or different and each is H, C₁ -C₆ -alkyl or substituted or unsubstituted phenyl, --CO--N(R⁷)₂, where the radicals R⁷ are identical or different and each is H or C₁ -C₄ -alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₁₀ -alkoximino-C₁ -C₂ -alkyl, aryl, aryloxy, benzyloxy, or C₃ -C₆ -cycloalkyl, or R³ and R⁴ together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted, or R³ and R⁴ may be halogen, and "aryl", alone or as part of another radical, is phenyl, naphthyl, or anthryl.
 6. A process for combating fungi, comprising contacting the fungi, or the materials, plants or seed threatened by fungus attack, or the soil, with a fungicidally effective amount of a compound of the formula I ##STR37## where X is CH--C₁ -C₄ -alkyl,Y is O, S or NR⁵, R¹, R² and R⁵ are H or C₁ -C₄ -alkyl, Z¹ and Z² are identical or different and each is H, halogen, methyl, methoxy or cyano, R³ and R⁴ are identical or different and each is hydrogen, cyano, straight-chain or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ --C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₅ -haloalkenyl, C₃ -C₆ -cycloalkenyl, C₃ -C₆ -halocycloalkenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₄ -alkylthio, benzylthio, C₁ -C₄ -alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C₁ -C₄ -alkoxylcarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁ -C₄ -alkyl, substituted or unsubstituted aryl-C₂ -C₄ -alkenyl, substituted or unsubstituted aryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted arylthio-C₁ -C₄ -alkyl, N(R⁶)₂, where the radicals R⁶ are identical or different and each is H, C₁ -C₆ -alkyl or substituted or unsubstituted phenyl, --CO--N(R⁷)₂, where the radicals R⁷ are identical or different and each is H or C₁ -C₄ -alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₁₀ -alkoximino-C₁ -C₂ -alkyl, aryl, aryloxy, benzyloxy, or C₃ -C₆ -cycloalkyl, or R³ and R⁴ together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted, or R³ and R⁴ may be halogen, and "aryl", alone or as part of another radical, is phenyl, naphthyl, or anthryl. 